How to Say “No” When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation'”)

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Matt_9509255413_99c9a1a118_z (Photo: Michael Matti)

The wisdom of life consists in the elimination of non-essentials.
– Lin Yutang

Discipline equals freedom.
Jocko Willink

This post will attempt to teach you how to say “no” when it matters most.

At the very least, it will share my story of getting there. It’s a doozy.

Here’s the short version:

I’m taking a long break from investing in new startups. No more advising, either. Please don’t send me any pitches or introductions, as I sadly won’t be able to respond. Until further notice, I am done. I might do the same with interviews, conferences, and much more.

Now, the longer version for those interested:

This post will attempt to explain how I think about investing, overcoming “fear of missing out” (FOMO), and otherwise reducing anxiety.

It’s also about how to kill the golden goose, when the goose is no longer serving you.

I’ll dig into one specifically hard decision — to say “no” to startup investing, which is easily the most lucrative activity in my life. Even if you don’t view yourself as an “investor”—which you are, whether you realize it or not—the process I used to get to no should be useful…

[Warning: If you’re bored by investment stuff, skip the next two bulleted lists.]

Caveat for any investing pros reading this:

  • I realize there are exceptions to every “rule” I use. Most of this post is as subjective as the fears I felt.
  • My rules might be simplistic, but they’ve provided a good ROI and the ability to sleep. Every time I’ve tried to get “sophisticated,” the universe has kicked me in the nuts.
  • Many startup investors use diametrically opposed approaches and do very well.
  • There are later-stage investments I’ve made (2-4x return deals) that run counter to some of what’s below (e.g. aiming for 10x+), but those typically involve a discount to book value, due to distressed sellers or some atypical event.
  • Many concepts are simplified to avoid confusing a lay audience.

Related announcements:

  • I will continue working closely with my current portfolio of startups. I love them and believe in them.
  • I will be returning all unallocated capital in my private Stealth Fund on AngelList. If you’re an investor in that fund, you’ll be getting your remaining money back. My public Syndicate will remain in place for later re-entry into the game.

So, why am I tapping out now and shifting gears?

Below are the key questions I asked to arrive at this cord-cutting conclusion.  I revisit these questions often, usually every month.

I hope they help you remove noise and internal conflict from your life.

The Road to No

ARE YOU DOING WHAT YOU’RE UNIQUELY CAPABLE OF, WHAT YOU FEEL PLACED HERE ON EARTH TO DO? CAN YOU BE REPLACED?

I remember a breakfast with Kamal Ravikant roughly one year ago.

Standing in a friend’s kitchen downing eggs, lox, and coffee, we spoke about our dreams, fears, obligations, and lives. Investing had become a big part of my net-worth and my identity. Listing out the options I saw for my next big moves, I asked him if I should raise a fund and become a full-time venture capitalist (VC), as I was already doing the work but trying to balance it with 5-10 other projects. He could sense my anxiety. It wasn’t a dream of mine; I simply felt I’d be stupid not to strike while the iron was hot.

He thought very carefully in silence and then said: “I’ve been at events where people come up to you crying because they’ve lost 100-plus pounds on the Slow-Carb Diet. You will never have that impact as a VC. If you don’t invest in a company, they’ll just find another VC. You’re totally replaceable.”

He paused again and ended with, “Please don’t stop writing.”

I’ve thought about that conversation every day since.

For some people, being a VC is their calling and they are the Michael Jordan-like MVPs of that world. They should cultivate that gift. But if I stop investing, no one will miss it. In 2015, that much is clear. There have never been more startup investors, and–right along with them–founders basing “fit” on highest valuation and previously unheard of terms. There are exceptions, of course, but it’s crowded. If I exit through the side door, the startup party will roll on uninterrupted.

Now, I’m certainly not the best writer in the world. I have no delusions otherwise. People like John McPhee and Michael Lewis make me want to cry into my pillow and brand “Poser” on my forehead.

BUT… if I stop writing, perhaps I’m squandering the biggest opportunity I have—created through much luck—to have a lasting impact on the greatest number of people. This feeling of urgency has been multiplied 100-fold in the last two months, as several close friends have died in accidents no one saw coming. Life is fucking short. Put another way: a long life is far from guaranteed. Nearly everyone dies before they’re ready.

I’m tired of being interchangeable, no matter how lucrative the game. Even if I’m wrong about the writing, I’d curse myself if I didn’t give it a shot.

Are you squandering your unique abilities? Or the chance to find them in the first place?

HOW OFTEN ARE YOU SAYING “HELL, YEAH!”? 

Philosopher-programmer Derek Sivers is one of my favorite people.

His incisive thinking has always impressed me, and his “hell, yeah!” or “no” essay has become one of my favorite rules of thumb. From his blog:

Those of you who often over-commit or feel too scattered may appreciate a new philosophy I’m trying: If I’m not saying “HELL YEAH!” about something, then I say no.

Meaning: When deciding whether to commit to something, if I feel anything less than, “Wow! That would be amazing! Absolutely! Hell yeah!” – then my answer is no. When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”

We’re all busy. We’ve all taken on too much. Saying yes to less is the way out.

To become “successful,” you have to say “yes” to a lot of experiments.  To learn what you’re best at, or what you’re most passionate about, you have to throw a lot against the wall.

Once your life shifts from pitching outbound to defending against inbound, however, you have to ruthlessly say “no” as your default. Instead of throwing spears, you’re holding the shield.

From 2007-2009 and again from 2012-2013, I said yes to way too many “cool” things. Would I like to go to a conference in South America? Write a time-consuming guest article for a well-known magazine? Invest in a start-up that five of my friends were in? “Sure, that sounds kinda cool,” I’d say, dropping it in the calendar. Later, I’d pay the price of massive distraction and overwhelm. My agenda became a list of everyone else’s agendas.

Saying yes to too much “cool” will bury you alive and render you a B-player, even if you have A-player skills. To develop your edge initially, you learn to set priorities; to maintain your edge, you need to defend against the priorities of others.

Once you reach a decent level of professional success, lack of opportunity won’t kill you. It’s drowning in 7-out-of-10 “cool” commitments that will sink the ship.

These days, I find myself saying “Hell, yes!” less and less with new startups. That’s my cue to exit stage left, especially when I can do work I love (e.g. writing) with 1/10th the energy expenditure.

I need to stop sowing the seeds of my own destruction.

HOW MUCH OF YOUR LIFE IS MAKING VERSUS MANAGING? HOW DO YOU FEEL ABOUT THE SPLIT?

One of my favorite time-management essays is “Maker’s Schedule, Manager’s Schedule” by Paul Graham of Y Combinator fame. Give it a read.

As Brad Feld and many others have observed, great creative work isn’t possible if you’re trying to piece together 30 minutes here and 45 minutes there. Large, uninterrupted block of time — 3-5 hours minimum — create the space needed to find and connect the dots. And one block per week isn’t enough.  There has to be enough slack in the system for multi-day CPU-intensive synthesis. For me, this means at least 3-4 mornings per week where I am in “maker” mode until at least 1pm.

If I’m in reactive mode, maker mode is all but impossible. Email and texts of “We’re overcommitted but might be able to squeeze you in for $25K. Closing tomorrow. Interested?” are creative kryptonite.

I miss writing, creating, and working on bigger projects. YES to that means NO to any games of whack-a-mole.

WHAT BLESSINGS IN EXCESS HAVE BECOME A CURSE? WHERE DO YOU HAVE TOO MUCH OF A GOOD THING?

In excess, most things take on the characteristics of their opposite. Thus:

Pacifists become militants.
Freedom fighters become tyrants.
Blessings become curses.
Help becomes hinderance.
More becomes less.

To explore this concept more, read up on Aristotle’s golden mean.

In my first 1-2 years of angel investing, 90%+ of my bets were in a tiny sub-set of startups. The criteria were simple:

  • Consumer-facing products or services
  • Products I could be a dedicated “power user” of, products that scratched a personal itch
  • Initial target demographic of 25-40-year old tech-savvy males in big US cities like SF, NYC, Chicago, LA, etc. (allowed me to accelerate growth/scaling with my audience)
  • <$10M pre-money valuation
  • Demonstrated traction and consistent growth (not doctored with paid acquisition).
  • No “party rounds”—crowded financing rounds with no clear lead investor. Party rounds often lead to poor due diligence and few people with enough skin in the game to really care.

Checking these boxes allowed me to add a lot of value quickly, even as relatively cheap labor (i.e. I took a tiny stake in the company). Shopify is a great example, which you can read about here (scroll down).

My ability to help spread via word of mouth, and I got what I wanted: great “deal flow.” Deals started flowing in en masse from other founders and investors.

Fast forward to 2015, and great deal flow is now paralyzing the rest of my life.  I’m drowning in inbound.

Instead of making great things possible in my life, it’s preventing great things from happening.

I’m excited to go back to basics, and this requires cauterizing blessings that have become burdens.

WHY ARE YOU INVESTING, ANYWAY?

For me, the goal of “investing” has always been simple: to allocate resources (e.g. money, time, energy) to improve quality of life. This is a personal definition, as yours likely will be.

Some words are so overused as to have become meaningless.  If you find yourself using nebulous terms like “success,” “happiness,” or “investing,” it pays to explicitly define them or stop using them. “What would it look like if I had (or won at) ___ ?” helps. Life favors the specific ask and punishes the vague wish.

So, here: to allocate resources (e.g. money, time, energy) to improve quality of life.

This applies to both the future and the present. I am willing to accept a mild and temporary 10% decrease in current quality of life (based on morale in journaling) for a high-probability 10x return, whether the ROI comes in the form of cash, time, energy, or otherwise. That could be a separate blog post, but conversely:

An investment that produces a massive financial ROI but makes me a complete nervous mess, or causes insomnia and temper tantrums for a long period of time, is NOT a good investment.

I don’t typically invest in public stocks for this reason, even when I know I’m leaving cash on the table. My stomach can’t take the ups and downs, but—like drivers rubbernecking to look at a wreck—I seem incapable of not looking. I will compulsively check Google News and Google Finance, despite knowing it’s self-sabotage. I become Benjamin Graham’s Mr. Market. As counter-examples, friends like Kevin Rose and Chris Sacca have different programming and are comfortable playing in that sandbox. They can be rational instead of reactive.

Suffice to say — For me, a large guaranteed decrease in present quality of life doesn’t justify a large speculative return.

One could argue that I should work on my reactivity instead of avoiding stocks. I’d agree on tempering reactivity, but I’d disagree on fixing weaknesses as a primary investment (or life) strategy.

All of my biggest wins have come from leveraging strengths instead of fixing weaknesses. Investing is hard enough without having to change your core behaviors. Don’t push a boulder up a hill just because you can.

Public market sharks will eat me alive in their world, but I’ll beat 99% of them in my little early-stage startup sandbox. I live in the middle of the informational switch box and know the operators.

From 2007 until recently, I paradoxically found start-up investing very low-stress. Ditto with some options trading. Though high-risk, I do well with binary decisions. In other words, I do a ton of homework and commit to an investment that I cannot reverse. That “what’s done is done” aspect allows me to sleep well at night, as there is no buy-sell choice for the foreseeable future. I’m protected from my lesser, flip-flopping self. That has produced more than a few 10-100x investments.

In the last two years, however, my quality of life has suffered.

As fair-weather investors and founders have flooded the “hot” tech scene, it’s become a deluge of noise. Where there were once a handful of micro VCs, for instance, there are now hundreds. Private equity firms and hedge funds are betting earlier and earlier. It’s become a crowded playing field. Here’s what that has meant for me personally:

  • I get 50-100 pitches per week. This creates an inbox problem, but it gets worse, as…
  • Many of these are unsolicited “cold intros,” where other investors will email me and CC 2-4 founders with “I’d love for you to meet A, B, and C” without asking if they can share my e-mail address
  • Those founders then “loop in” other people, and it cascades horribly from there. Before I know it 20-50 people I don’t know are emailing me questions and requests.
  • As a result, I’ve had to declare email bankruptcy twice in the last six months. It’s totally untenable.

Is there a tech bubble? That question is beyond my pay grade, and it’s also beside the point.

Even if I were guaranteed there would be no implosion for 3-5 years, I’d still exit now. Largely due to communication overload, I’ve lost my love for the game.  On top of that, the marginal minute now matters more to me than the marginal dollar.

But why not cut back 50%, or even 90%, and be more selective?  Good question. That’s next…

ARE YOU FOOLING YOURSELF WITH A PLAN FOR MODERATION?

The first principle is that you must not fool yourself and you are the easiest person to fool.
– Richard P. Feynman

Where in your life are you good at moderation? Where are you an all-or-nothing type? Where do you lack a shut-off switch? It pays to know thyself.

The Slow-Carb Diet succeeds where other diets fail for many reasons, but the biggest is this: It accepts default human behaviors versus trying to fix them. Rather than say “don’t cheat” or “you can no longer eat X,” we plan weekly “cheat days” (usually Saturdays) in advance. People on diets will cheat regardless, so we mitigate the damage by pre-scheduling it and limiting it to 24 hours.

Outside of cheat days, slow carbers keep “domino foods” out of their homes. What are domino foods? Foods that could be acceptable if humans had strict portion control, but that are disallowed because practically none of us do. Common domino foods include:

  • Chickpeas
  • Peanut butter
  • Salted cashews
  • Alcohol

Domino triggers aren’t limited to food. For some people, if they play 15 minutes of World of Warcraft, they’ll play 15 hours. It’s zero or 15 hours.

For me, startups are a domino food.

In theory, “I’ll only do one deal a month” or “I’ll only do two deals a quarter” sound great, but I’ve literally NEVER seen it work for myself or any of my VC or angel friends. Sure, there are ways to winnow down the pitches. Yes, you can ask “Is this one of the top 1-2 entrepreneurs you know?” to any VC who intro’s a deal and reject any “no”s. But what if you commit to two deals a quarter and see two great ones the first week? What then? If you invest in those two, will you be able to ignore every incoming pitch for the next 10 weeks?

Not likely.

For me, it’s all or nothing. I can’t be half pregnant with startup investing.  Whether choosing 2 or 20 startups per year, you have to filter them from the total incoming pool.

If I let even one startup through, another 50 seem to magically fill up my time (or at least my inbox). I don’t want to hire staff for vetting, so I’ve concluded I must ignore all new startup pitches and intros.

Know where you can moderate and where you can’t.

YOU SAY “HEALTH IS #1″…BUT IS IT REALLY?

After contracting Lyme disease and operating at ~10% capacity for nine months, I made health #1. Prior to Lyme, I’d worked out and eaten well, but when push came to shove, “health #1” was negotiable. Now, it’s literally #1. What does this mean?

If I sleep poorly and have an early morning meeting, I’ll cancel the meeting last-minute if needed and catch up on sleep. If I’ve missed a workout and have a con-call coming up in 30 minutes? Same. Late-night birthday party with a close friend? Not unless I can sleep in the next morning. In practice, strictly making health #1 has real social and business ramifications. That’s a price I’ve realized I MUST be fine paying, or I could lose weeks or months to sickness or fatigue.

Making health #1 50% of the time doesn’t work. It’s absolute — all or nothing. If it’s #1 50% of the time, you’ll compromise precisely when it’s most important.

The artificial urgency common to startups makes mental and physical health even more challenging. I’m tired of unwarranted last-minute “hurry up and sign” emergencies and related fire drills. It’s a culture of cortisol.

ARE YOU OVER-CORRELATED?

[NOTE: Two investors friends found this bullet slow, as they’re immersed in similar subjects. Feel free to skip if it drags on, but I think there are a few important novice concepts in here.]

“Correlated” means that investments tend to move up or down in value at the same time.

As legendary hedge fund manager Ray Dalio told Tony Robbins: “It’s almost certain that whatever you’re going to put your money in, there will come a day when you will lose 50 percent to 70 percent.” It pays to remember that if you lose 50%, you need a subsequent 100% return to get back to where you started. That math is tough.

So, how to de-risk your portfolio?

Many investors “rebalance” across asset classes to maintain certain ratios (e.g. X% in bonds, Y% in stocks, Z% in commodities, etc.). If one asset class jumps, they liquidate a part of it a buy more of lower performing classes. There are pros and cons to this, but it’s common practice.

From 2007-2009, during the “real-world MBA” that taught me to angel invest, <15% of my liquid assets were in startups. I was taking a barbell approach to investing. But most startups are illiquid. I commonly can’t sell shares until 7-12 years after I invest, at least for my big winners to date. What does that mean? In 2015, startups comprise more than 80% of my assets. Yikes!

Since I can’t sell, the simplest first step for lowering stress is to stop investing in illiquid assets.

I’ve sold large portions of liquid stocks—mostly early start-up investments in China–to help get me to “sleep at night” levels, even if they are lower than historical highs of the last 6-12 months. Beware of anchoring to former high prices (e.g. “I’ll sell when it gets back to X price per share…”). I only have 1-2 stock holdings remaining.

Some of you might suggest hedging with short positions, and I’d love to, but it’s not my forte. If you have ideas for doing so without huge exposure or getting into legal gray areas, please let me know in the comments.

In the meantime, the venture capital model is mostly a bull market business. Not much shorting opportunity. The best approximation I’ve seen is investing in businesses like Uber, which A) have a lot of international exposure (like US blue chips), and B) could be considered macro-economically counter-cyclical. For instance, it’s conceivable a stock market correction or crash could simultaneously lead fewer people to buy cars and/or more people to sign up as Uber drivers to supplement or replace their jobs. Ditto with Airbnb and others that have more variable than fixed costs compared to incumbents (e.g. Hilton).

WHAT’S THE RUSH? CAN YOU “RETIRE” AND COME BACK?

I’m in startups for the long game. In some capacity, I plan to be doing this 20+ years from now.

The reality: If you’re spending your own money, or otherwise not banking on management fees, you can wait for the perfect pitches, even if it takes years. It might not be the “best” approach, but it’s enough. To get rich beyond your wildest dreams in startup investing, it isn’t remotely necessary to bet on a Facebook or Airbnb every year. If you get a decent bet on ONE of those non-illusory, real-business unicorns every 10 years, or if you get 2-3 investments that turn $25K into $2.5M, you can retire and have a wonderful quality of life. Many would argue that you need to invest in 50-100 startups to find that one lottery ticket. Maybe. I think it’s possible to narrow the odds quite a bit more, and a lot of it is predicated on maintaining stringent criteria; ensuring you have an informational, analytical, or behavioral advantage; and TIMING.

Most of my best investments were made during the “Dot-com Depression” of 2008-2009 (e.g. Uber, Shopify, Twitter, etc.), when only the hardcore remained standing on a battlefield littered with startup bodies. In lean times, when startups no longer grace magazine covers, founders are those who cannot help but build a company. LinkedIn in 2002 is another example.

HOWEVER… This doesn’t mean there aren’t great deals out there.  There are. Great companies are still built during every “frothy” period.

The froth just makes my job and detective work 10x harder, and the margin of safety becomes much narrower.

[Tim: Skip this boxed text if the concept of “margin of safety” is old news to you.]

Think of the “margin of safety” as wiggle room.

Warren Buffett is one of the most successful investors of the 20th century and a self-described “value investor.” He aims to buy stocks at a discount (below intrinsic value) so that even with a worst-case scenario, he can do well. This discount is referred to as the “margin of safety,” and it’s the bedrock principle of some of the brightest minds in the investing world (e.g., Seth Klarman). It doesn’t guarantee a good investment, but it allows room for error.  Back in the startup world…

I want each of my investments, if successful, to have the ability to return my “entire fund,” which is how much capital I’ve earmarked for startups over two years, for instance. This usually means potential for a minimum 10X return. That 10X minimum is an important part of my recipe that allows margin for screw ups.

For the fund-justifying ROI to have a snowball’s chance in hell of happening, I must A) know basic algebra to ensure my investment amounts (check sizes) permit it, and B) avoid companies that seem overpriced, where the 10x price is something the world has never seen before (i.e. no even indirect comparables, or tenable extrapolations from even an expanded market size).

If you throw low-due-diligence Hail Mary’s everywhere and justify it with “they could be the next Uber!”, you will almost certainly be killed by 1,000 slow-bleeding $25K paper cuts. Despite current euphoria, applying something like Pascal’s Wager to startups is a great way to go broke.

Good startup investors who suggest being “promiscuous” are still methodical.

It’s popular in startup land to talk about “moonshots”—the impossibly ambitious startups that will either change the world or incinerate themselves into star dust.

I’m a fan of funding ballsy founders (which includes women), and I want many moonshots to be funded, but here’s the reality of my portfolio: as I’ve signed the investment docs for every big success I’ve had, I’ve always thought, “I will never lose money on this deal.”

The “this will be a home run or nothing” deals usually end up at nothing. I’m not saying such deals can’t work, but I try not to specialize in them.

These days, the real unicorns aren’t the media darlings with billion-dollar valuations. Those have become terrifyingly passé. The unicorns are the high-growth startups with a reasonable margin of safety.

Fortunately, I’m not in a rush, and I can wait for the tide to shift.

If you simply wait for blood in the streets, for when true believers are the only ones left, you can ensure come-hell-or-high-water founders are at least half of your meetings.

It might be morbid, but it’s practical.

My Last Deals For A While

It’s still a great time to invest in companies… but only if you’re able to A) filter the signal from the noise, B) say no to a lot of great companies whose investors are accepting insane terms, and C) follow your own rules. Doing all three of these requires a fuck-ton of effort, discipline, and systems. I prefer games with better odds.

There are a few deals you’ll see in the upcoming months, which I committed to long ago. These are not new deals.

They are current companies in which I’m filling my pro-rata, or companies postponing funding announcements until they’re most helpful (e.g. launching publicly). Separately, I work closely with the Expa startup lab and will continue to do so. They are largely able to insulate themselves from madness, while using and refining an excellent playbook.

Are You Having a Breakdown or a Breakthrough? A Short How-To Guide

“Make your peace with the fact that saying ‘no’ often requires trading popularity for respect.”
– Greg McKeown, Essentialism

If you’re suffering from a feeling of overwhelm, it might be useful to ask yourself two questions:

– In the midst of overwhelm, is life not showing me exactly what I should subtract?
– Am I having a breakdown or a breakthrough?

As Marcus Aurelius and Ryan Holiday would say, “The obstacle is the way.” This doesn’t mean seeing problems, accepting them, and leaving them to fester. Nor does it mean rationalizing problems into good things. To me, it means using pain to find clarity. Pain–if examined and not ignored–can show you what to excise from your life.

For me, step one is always the same: write down the 20% of activities and people causing 80% or more of your negative emotions.

My step two is doing a “fear-setting” exercise on paper, in which I ask and answer “What is really the worst that could happen if I did what I’m considering? And so what? How could I undo any damage?”

Below is a real-world example: the journal page that convinced me to write this post and kickstart an extended startup vacation.

The questions were “What is really the worst that could happen if I stopped angel investing for a minimum of 6-12 months? Do those worse-case scenarios really matter? How could I undo any potential damage? Could I do a two-week test?”

As you’ll notice, I made lists of the guaranteed upsides versus speculative downsides. If we define “risk” as I like to—the likelihood of an irreversible negative outcome—we can see how stupid (and unnecessarily painful) all my fretting and procrastination was. All I needed to do was put it on paper.

Below is a scan of the actual page.  Click here for an enlarged version.

Further below is a transcribed version (slightly shorter and edited). For a full explanation of how and why I use journaling, see this post.  In the meantime, this will get the point across:

Journal_Startup_Vacation

Transcription:

“The anxiety is mostly related to email and startups: new pitches, new intros, etc.

Do a 2-week test where “no” to ALL cold intros and pitches?

Why am I hesitant? For saying “no” to all:

PROS:
– 100% guaranteed anxiety reduction
– Feeling of freedom
– Less indecision, less deliberation, so far more bandwidth for CREATING, for READING, for PHYSICAL [TRAINING], for EXPERIMENTS.

CONS (i.e. why not?):
– Might find the next Uber (<10% chance) — Who cares? Wouldn’t materialize for 7-9 years. If Uber pops (IPO), it won’t matter.
– Not get more deals. But who cares?
* Dinner with 5 friends fixes it.
* One blog post fixes it. [Here’s an example from 2013 that helped me find Shyp and co-lead their first round]
* NONE of my best deals (Shyp, Shopify, Uber, Twitter, Facebook, Evernote, Alibaba, etc.) came from cold intros from acquaintances.

If try 2 weeks, how to ensure successful:
– I don’t even see interview or [new] startup emails
– No con-calls. [Cite] “con call vacation” –> push to email or EOD [end-of-day review with assistant]
– Offer [additional] “office hours” on Fridays [for existing portfolio]?

I ultimately realized: If I set up policies to avoid new startups for two weeks, the systems will persist. I might as well make it semi-permanent and take a real “startup vacation.”

What do you need a vacation from?

My Challenge To You: Write Down The “What If”s

“I am an old man and I have known a great many troubles, but most of them never happened.”
– Mark Twain

“He who suffers before it is necessary suffers more than is necessary.”
– Seneca

Tonight or tomorrow morning, take a decision you’ve been putting off, and challenge the fuzzy “what if”s holding you hostage.

If not now, when? If left at the status quo, what will your life and stress look like in six months? In one year? In three years? Who around you will also suffer?

I hope you find the strength to say no when it matters most. I’m striving for the same, and only time will tell if I pull it off.

What will I spend my time on next? More crazy experiments and creative projects, of course.  To hear about them first, sign up for my infrequent newsletter. Things are going to get nuts.

But more important — how could you use a new lease on life?

To surf, like this attorney who quit the rat race? To travel with your family around the world for 1,000+ days, like this?  To learn languages or work remotely in 20+ countries while building a massive business? It’s all possible. The options are limitless…

So start by writing them down. Sometimes, it takes just a piece of paper and a few questions to create a breakthrough.

I look forward to hearing about your adventures.

Posted on: October 29, 2015.

Please check out Tools of Titans, my new book, which shares the tactics, routines, and habits of billionaires, icons, and world-class performers. It was distilled from more than 10,000 pages of notes, and everything has been vetted and tested in my own life in some fashion. The tips and tricks in Tools of Titans changed my life, and I hope the same for you. Click here for sample chapters, full details, and a Foreword from Arnold Schwarzenegger!

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Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration)

294 comments on “How to Say “No” When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation'”)

  1. Good for you. For what it’s worth, I’ve been LOVING the podcasts. Not just the info (though that’s been invaluable of itself), but the Socratic questioning. I met you years ago in a pub in London when doing your Book tour on 4HWW (which triggered a 6 month trip round Latin America with my wife and four kids, one still in nappies), but reading and listening to your latest work, it’s like someone different. I am astonished watching your learning, and have derived enormous vicarious value from it.

    For instance, I’ve personally interviewed over 1000 people, so thought myself a dab hand at questioning. But after devouring many (not all) of your podcasts, I feel like a rank amateur! I’ve suddenly found myself questioning far more more precisely, and getting far more useful answers. So time back on your creativity, experimentation and writing would be most welcome.

    Now to learn that ‘no’ trick…….

    Like

  2. Tim

    Believe it or not. I am a high achiever. The highest I know Of all my mates… Yet I feel lost and confused when it comes to the future and what my life holds.

    It’s short lived and I try for the present but you are one of the only mediums that gives me clarity.

    I use the headspace app. I follow you religiously and I hope one day…. It just clicks.

    Don’t leave us for the money bro. Let’s roll physically or mentally one day. Either way you’re the man X

    Like

  3. Tim,
    I just wanted to convey a deep and rare respect for someone I have never met. I have been following your blog since I read the 4 Hour Work Week in 2008. For someone who in all likelihood doesn’t need the money and could go take a permanent sabbatical in Margaritaville, it is most inspiring the amount you give back. I want to thank you for the motivation I receive from seeing someone who is not only trying to constantly improve themselves, but whom also shares freely all they have learned.
    While I have been inspired and educated by your teachings, I have until now failed to break free from the many trappings of this world and my own internal resistance. Through recent health and financial crisis I have barely been keeping my head above water, all the while watching great people like yourself continue to better this cruel and confusing world.
    Today I give myself 30 days to change my life and to make use of the wealth of knowledge I have absorbed. Knowledge disseminated by yourself, others you have learned from and those who have benefited from those lessons.
    I hope that as part of the 30 day mission I have given myself and as part of the respect I have for what you do, that this will be the first of more interaction with you and your community. I just wanted to start my endeavour with thanks to someone who has and continues to inspire me. Keep up the good work, Tim. There are those who greatly appreciate it.

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  4. Slow clap Tim, slow clap. I had a sense this was coming too as I noticed a shift in your attitude about what was becoming more important to you. It’s funny and uncanny timing for me as I was just thinking about applying for another job for higher pay and leaving my passion were I am almost I irreplaceable, but have hesitated as I love being a total expert in something and don’t just want to be a generic manager. Your post has allowed me to feel good about my decision to carry on being the passionate expert in my area. I wish you all the best. You’re still my life guru Tim, so I eagerly await your next adventure. 😀

    Like

  5. Tim, My first time ever writing … this blog brought a tear to my eye.

    Here is what I want to say: please don’t stop writing. Best adjective to describe you is as one of the most ‘genuine’ writers out there. You are one of two blogs I allow to download (as in ‘no’). I have read work week and body, not yet to the food book being the proud owner of several hundred cook books.

    I am not in your demographic being a 72 year old woman (and late bloomer obviously) but am always inspired by you. And to your Mom and gout, I share that affliction and have held it at bay for several years with an alkaline diet – sugar is the most acid for me.

    Future writing idea since I have massive info and questions about aging: let us do a book together.
    Many thanks to you!!
    Bonnie

    Liked by 2 people

  6. Hey Tim, Great article. I have also been pondering this question for some time. Not about investing but about just saying no to more things in life. I have unsubscribed to many lists recently only reading a few blogs that I give me the most bang for my buck. I have also made a pretty big decision recently to stop running competitively and coaching after more than 20 years. To stop coaching and walk away from helping my athletes was very hard. I felt like I was letting them down. But then I realised I was giving so much and it was time to give to myself. I am now travelling the world solo.

    Re doing what you love. That seems to come up all around the world to be successful. I have a slightly different twist on that. I believe in doing what your personality is suited to. Heres my basic analogy. You may love coffee and the whole coffee industry. So you decide to get a job as a barista. You become the best barista in town but you still don’t love what you do. Maybe, your like me and don’t love interacting with humans everyday. Maybe you can still love coffee but can become a coffee roaster instead. My point is sometimes our personalities aren’t suited to the things we think we love

    I would suggest I hear a little bit of this come through in your writing. Your personality is more suited to writing and being a little more alone. You can control it more, interact with people less and work more on your own terms as opposed to the demand of companies you advise and invest in. Stick to what your personality is suited to and it will become what you love. 🙂

    keep up the writing.

    Like

  7. Thanks Tim. RE your recent 5 bullet friday. You are comparing 30g waking protein with intermittent fasting for muscle growth. Great question as I know you raised this with Dr Peter Thia (sic) and I’ve wondered the same for a while. You said the Bluebonnet was clearly the winner so far? What the hell is a bluebonnet? Given that you are a writer and wishing to always improve..in a concise clear little list of bullet points, I was upset you chose to use a totally obscure colloquial reference – possibly heavily demographic dependent – as the answer to a question?!!! i begrudingly tried an internet search – begrudingly because I shouldn’t feel I have to, when you’re not writing about a specialist topic (Eg investing, where you can expected to use phrases I won’t understand) – but even the internet didn’t help! Theres several plants and the UN and something else all called a bluebonnet. Lovingly, respectfully Timmy, write in a way that will make still make sense in 1, 20 , 40, 100 years and you’ll go even further
    (posting here because this post is about focusing on your writing, the 5 bullet friday post refers to this post – and I dont use twitter and facebook because I’m old school 😉 YO

    Liked by 1 person

  8. Tim. Thank you. You nailed it. Quick story – Last year I was 29 year old at the height of my career, in my 2nd year as c-level exec for a pretty large firm (by far youngest exec in my industry). I thought I was happy, but I felt shallow like something was missing. I knew I was doing other people’s work and adding very little to the world. I knew I was fooling myself to stay on the path of making more, consuming more, and wanting more.

    Long story short, there’s probably 25 books and 100 podcasts that I’ve read/listened/studied that have contributed to turning my life around, but I can tell you that few people were more instrumental than you.

    Today I’m 30 years old, 1 year removed from leaving my job and working to take my life back. I couldn’t be happier. My life is better, the people in my life have been positively affected, and I know that my impact on the world will be exponentially greater now that my priorities are back in control. Thanks to you.

    This latest post crystallizes to me how important you are to my continuede awakening.

    “Give me a lever long enough and a fulcrum on which to place it, and I shall move the world.” Cheesy but true: you are a great lever and people like me are your fulcrum. KEEP WRITING, KEEP TEACHING, KEEP INSPIRING.

    Sorry, I would’ve wrote a shorter post but I didn’t have enough time.

    Liked by 1 person

  9. Tim,

    Absolutely get your need to take a prolonged vacation from what may bring you wealth but not joy. May we all have that courage.

    Your decision likely is a benefit to me as presumably you will write and teach more.

    My question – You mention you don’t want to hire staff to vet deals. Once your post VC sabbatical why not leverage your brand and hire staff to vet deals and winnow the nonsense?

    Best wishes in all.

    JWH

    Like

  10. Hey Tim I just wanted to say congratulations on making this move. I have hard copies of all your books. Yours is the only blog I read regularly. Yours is the only podcast I listen to regularly. I’ve used the 4HWW to make a huge career change, used the 4HBody to put in 12 pounds of muscle in 6 weeks, and have used the 4HourChef to train myself in skill acquisition and of course, make delicious lamb shank and rosemary pistachio cookies.

    All this to say, I’m really glad that you’re out writing and creating. When the 4HourChef came out it seemed unclear whether or not you were planning on continuing to write, and that made me a little sad. I was, and now am, looking forward to seeing what comes of your new decision.

    Un fuerte abrazo,
    Faiyam

    Like

  11. Your writing and experiments have been of huge benefit to so many people. For me, life changing. Your podcasts have introduced me to very interesting people and great ideas. I have learned so much from your work. Take a break, look after your health and recharge but please keep writing and teaching.

    Liked by 1 person

  12. I loved that you used cauterize as a verb. That aside, if I could be so bold as to suggest: you need catharsis. To my mind the mountains bring a sharp catharsis that no Malbec or gorgeous woman ever could. In Banff/Canmore right now, we are in the opening weekend of the Mountain Film Festival, with both Alex Honnold, AND Jimmy Chin here to discuss their movies. There’s snow in the backcountry, sunny afternoons, and yoga teachers that will kick your ass both physically and psychologically. Day-to-day life might not be slow-carb compliant, but the crisp mountain air will fill you with leanness and life. All the best, and thank-you for being candid,
    ~Krista

    Liked by 1 person

  13. I gained so many insights about my own life and activity flow from this blogpost. I will share it with a friend who has also recently started to implement 80/20 more into her personal life for the long-haul.

    The part about finding the place where you are irreplaceable in terms of impact resonates with me the most. Yes, please, never stop writing.

    Liked by 1 person

  14. Actually saying “no” to anything but “hell yeahs” is a powerful thing. Left and right I see people like Tim embracing this path. What moved me the most was the interview with Lady Gaga about this and other things. It was what liberated her more then meditation or any other way of dealing with stress and anxiety.

    Here is the short passage:

    But you really want to listen to the longer version:

    Jump to 8:00 if you re in a hurry.

    Best,
    Elmar

    Like

  15. Hi Tim

    I’m so glad that you found yourself back on your road, congrats

    I’m a french guy and I quite sure to be one of the first in France to follow you for so many years now

    I also might be able to write you a book (hell yeah just for you man) about what you’re living because there’s a point you always miss and never talk about (And I can’t do it either in public), and why it’s so ? Because I’m like you a true researcher of life.

    Now that you’ll finally have some time, I respectfully invite you in my hometown Saint-Malo (Britanny, France #3 best cities on airbnb France 😉 )
    I wanted to do so for at least 5 years, never did it because you became like a “star”, but now is the time, come visit me and you won’t regret it (you can also learn french ^^ how good is that cherry ?)

    This is an open invitation with no time limitation ^^ and of course we can just chat as well by email

    My intentions are pure (not business related, I have 2 companies already, not money related I have some and don’t need it, just pure thinking for the beauty of it)

    Bye Tim and I hope to read or see you soon

    Gwen
    Ps:sorry for my english 😉

    Liked by 1 person

  16. I love what Tim writes and the way he can be cool (experiments, insights, getting the edge and so on) and intelligent (this post). There’s somehow a feeling that often puts me on a different thought-track. Self-help, getting better, being more productive…produce a lot of stress. Fighting stress and anxiety using rules, stress management techniques and similar…produce some stress too. Wouldn’t it be better to just “be”? Take life less seriously, as if it isn’t a race? Being more ZOrba and less like the narrator. I see many great smart intelligent horses that run furiously towards the carrot stuck to their heads. (Don’t get me wrong, I am one of them. Ok, maybe not the smartest one).

    Last night I went to see Neil Strauss latest book’s presentation. The night was excellent, but before he got on stage I had a quick chat with guys in the audience. People trying to speed up speed reading (“So I can skim/read 10 books per week”), people believing that “it’s not what you know, it’s not who you know, but it’s how you can use NLP so people can know you”. People saying “we are not making any money, but being an entrepreneur has made me a better person because now I know how to allocate time to people I love”. Wow.

    I don’t know, maybe it’s just me. Maybe I grew up in a country that wasn’t obsessed with ‘getting better’ (Italian current economy maybe proves me right, ha!), but after 10 years that I read it, I still believe that the story of the mexican fisherman holds a big truth.
    Or maybe we see the world in the exact same way, though using different cultural lenses.

    Like

  17. Tim,

    Enjoyed this article. For reference my favorite pieces are your longer articles and Podcasts. I am a Exec Dir of a non-profit for the last two years and have used many things I learned from you and your guests. Thank you. The thing I long for is a compiled bibliography of books your Podcast guests (and you) have recommended. Maybe there is such a list already?

    My best to you in all endeavors.

    Liked by 1 person

  18. This is an exceptional post reminding all of us once again the power in saying NO, so that we can live our own ideal lives. People and circumstances will steal your time and your life, if you let them. Saying NO is the first step to regaining control.

    We are doing this in our business to make certain we are only working with “Ideal Clients” that fit our specific profile. Others we will politely disengage to focus on those that pay us for what we do.

    Again, what is the worst that will happen?

    Liked by 1 person

  19. Insightful posts like this, along with the links, references, and asides, is your personal brand. It looks to me that can not help being that person – it’s wired – so it is what you should do as a priority and everything else gets done only to the extent that it supports or grows that one thing. IMHO.

    Liked by 1 person

  20. Hi! Tim, you inspire everyone who reads your posts to better a quality of life. Most of all you inspire me to be effective and invest in peace. I like it that I can be curious, question assumptions (create distinctions); its vicarious learning from your writing that gets me or anyone else for that matter to your posts. May you go from strength to strength in your writing, experimenting etc . God Bless You

    Liked by 1 person

  21. Ohhh, this may explain it. I have listened to many of your podcast episodes. You’re really good. But…

    I kept being curious about a very different tone and energy you seem to have with deeper thinkers (often older, but not always) guests versus Silcon Valley-alicious folk with more money and tactical advice than curiosity.

    I could be wrong, but I notice a different excitement (sincerity?) to the sound of your voice with these different guests. When you got more entrepreneur & tech-heavy, you were still good and enthusiastic, but your tone reveals less satisfaction and stimulation. It seems to go beyond whether you like the guest a lot or not.

    Money is awesome and necessary, so maybe this time-off post is prep for monetizing a decision. That’s cool, too. I’m curious about how people apply curiosity to designing their lives, how much they hedge for pivoting, how fame plays a role, and at what age (if any) does it no longer matter.

    Why comment? Curiosity.

    Like

  22. I notice that you write with crushed “e”s. that means you can have trouble listening to people. But you listened to your friend in the kitchen. Excellent thought process. I am, however, slightly concerned about your T stroke.

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  23. Awesome post mate, so true to the heart. I have been shedding a lot of layers myself lately to make room for the hell yes in my entrepreneurial journey. It’s comforting to know that an epic individual such as urself still feels the squeeze too. Never stop writing mate! Yieww 🙂

    Liked by 1 person

  24. Sit back with your glass of wine tonight, feel relaxed relief….enjoy!
    Thanks for all the interviews you do, good questions you ask, your inner journey sharing…I enjoy listening while I stack wood for the winter in rural Montana, do the dishes, and drive through the canyon and forest.

    Like

  25. I was super excited for you when you mentioned in the interview with Tara that you were thinking about cutting the startups strings. At first, I was mostly excited for your focus to return to writing, but now I wouldn’t care if you never produced another post!

    I might finally catch up!

    Happen to be in the middle of my own 2 years of living dangerously and saying no – wife and 3 young ones hanging with me – and while sometimes stressful, also incredibly enriching.

    All the best to you.

    Liked by 1 person

  26. I remember in one of your podcasts, the interviewee asked you back on what you would tell your 30 year old self, and you said “to chill the **** out”. Good to see you taking your own advice there! 😉

    Like

  27. The initial disappointment reading about your “retirement” quickly transposed to joy – Great decision and I applaud the direct and honest way you have communicated to your audience.

    I recently sold my house in Sydney, quit Banking and moved the family up to Coffs Harbour and am currently renovating our new house. Quality of life and happiness have increased exponentially for me, my wife and the kids. I am also excelling at sport (squash)

    Reading your books and listening to your podcasts helped to cultivate these seeds of happiness. Simple things resonate, ‘specialisation is for insects’, captain a ship…..I have never done plastering, carpentry or plumbing but I do have a support network from your book club, such as obstacle is the way or art of learning. I am very grateful for how you have (unknowingly) helped me – thank you.

    Have a happy break and give Australia a go, they have a saying “I wouldn’t be dead for quids…”

    Like

  28. Great post. There is more to life than the pursuit of MORE money, being minimalistic and spending time on the things you love helps reduce anxiety and leads to a happier and more fulfilled life.

    Like

  29. Great post. Last year my wife and I asked the question ‘How much is enough?’

    It’s amazing what you don’t need and how ‘the chase’ can become your life.

    The last 12 months has been transformation for us and we are happier and healthier than ever.

    Like

  30. Good effort! For me it takes 3 months of no noise before I can hear clearly again.

    Stage left has a sign above saying “no exit”, well fuck that! I know there is a door behind the sign and I’m taking it immediately.

    Good luck in saying NO! you’ll need it, but I hope you manage for the sake of your own health.

    Poetry?

    Like

  31. Hi Tim, loved this. Thank you. Totally where we are in our business and it makes so much sense. We have worked so hard to get to where we are that saying no seems alien to all those years we had to say yes just to stay in. As our energy has been expended more by doing this over the years the only way for us to carry on now is by saying no – and in turn make sure the business continue to grow with a small but clear market. Best article yet.

    Like

  32. Hey Tim, recent convert and loving beyond loving your content. Please don’t stop the podcasts – please. I get so much from them, and helps me feel if even just distantly, like I’m mixing with people so much smarter than me! BTW i want to say “no more’ to full time employment – soon Tim, soon. 🙂

    Like

  33. recently read and reread Essentialism (probably a book I picked up after listening to a podcast… yours perhaps?) Good to see that you are following that same advice. Always hard to say no, but look forward to seeing more of your works.

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  34. Your investing rules sound very similar to playing Poker! – ” If you throw low-due-diligence Hail Mary’s everywhere and justify it with “they could be the next Uber!”, you will almost certainly be killed by 1,000 slow-bleeding $25K paper cuts.”

    Like

  35. I’m glad that you are finally taking a break from investing in startups and doing what is probably your vocation in life, which is to help people live a better life via your writing about your lifestyle design experiments. I’ve always dreamed of doing what you’re doing and until I read you and faced a life-changing situation recently I wouldn’t be trying to fulfill my vocation right now. Thanks for waking me up to the wonderful possibilities in life.

    Like

  36. Perfect timing! I’ve enrolled in a really amazing course and am really wanting to do another great course. In my heart I know I cannot do them both justice but I was suffering from a FOMO moment – what if I never get the chance again to do the second course? I love that you named and crystallised the issue for me!

    Like

  37. Dear Tim, thanks for your email. It has come at an unusual time for me. I’ll just take it as a sign and leave it at that. I’m saddened too about losing my passion for my job in education, it’s all test scores and diagnostic reviews for me at present. I don’t understand any of your start up business investment info, but I do understand how you can become overwhelmed by OPS (other people’s stuff…). I’m going to heed your timely advice and step off the treadmill for a while, to find me again. I wish you all the best and thank you so much for your words. I know you have zillions who follow you, but your email and your reflections made me feel like your message was just for me. So thank you. Enjoy your new life. Hopefully I can join you soon…

    Like

  38. Thanks Tim. The timing of your practical yet soulful blog post for me couldn’t be better. I’m currently in the early stage (3 months) in a gap year from my startup adventures to try and re-find my creativity and passion. For the first time in my life I don’t know what’s next. Sitting idle is very hard for me and sirensong shiny objects everywhere. Your straight shooting advice at the least, helps me stay disciplined and fight off the fear demons that always try and creep in, and at the most, sends me on my journey to something phenomenal, energetic and impactful that I’d never touch had I stayed timid and chained to my old life. Thanks and adventurous travels bro!

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  39. Tim,
    You couldn’t possibly read all these comments, but this was, as most people wading in have said, a very good post. So I just had to add to it.

    I think you said you were backing off on podcast interviews as well, but I might have read that too fast. My commute will be impoverished if you do that.

    It is encouraging to know that rich folks like you (I know, compared to who) in some ways think like poor people like me. I have used a journal for years to write down worries, etc and always wondered if it was a mental crutch I needed to maintain my sanity and wondered if anyone else did it. It sure helps me cope with life so I guess it is a welcome crutch. It is also interesting and confirms my belief that rich people just have another set of problems. Instead of how am I going to stay off the street, it’s how can I deal with so much opportunity and stay true to myself. I think I would like a shot at some of those kind of problems.

    Listening and reading younger folks (I am 70) ideas really keeps me energized. You, Greenfield, and James Altucher are my core podcast addictions. Sure hope you keep those coming.

    Like

  40. Tim,

    This article is phenomenal. The blend of reference to great published work,
    unique new insights, twinned with your personal experience to illustrate make fantastic reading. Reminds me of the early stuff you wrote that first got me hooked.

    Thank you.

    G

    Like

  41. Hi Tim,
    I see the pain points you have. I am pretty sure other Angel Investors might be facing similar issues. If I may ask, If there is an Angel Investor Service such as filtering pitch decks, summarizing those that fit your investment style, and providing you with a one-page executive summary on those opportunities that are worthwhile pursuing, wouldn’t that alleviate your problem?

    Like

  42. IMO you’re right on track, Tim. I haven’t opened/read one of your newsletters since you wrote that post on suicide, because there didn’t seem to be enough depth. I’m about 1/2 way through a slow version of what you’re describing and it’s liberating. My health is returning and I’m narrowing down time allocated for “friends” to people I genuinely miss when they’re gone. Best wishes for success.

    Like

  43. Synchronicity! Just heard this on, who’d a thunk, an evangelical Christian radio show. (I stop in every once in a while to see if they speak to my heart) Of course they worded it: find out what God most wants you to do. Find out what energizes you most in the doing….The Universe knocking? Gonna give it a go. I’m amazed how often this is the case with your posts. Good on ya!

    Like

  44. Awesome article Tim! I’ve always told people that the thing you do best is focus & master things at rapid speed- which requires space & time. People LOVE when you create.

    Secondly, there is a false expectation in our society that wants you to continue to do something that you are world-class at just bc you can. When in the big picture it may have just been one path you were meant to go along for a period of time to accumulate experiences that prepare you for your next journey.

    One life many life’s times!

    Ed okeefe

    Ps: did kamal hug in only that way kamal can?

    Like

  45. Thanks, Tim.
    For me, this has been one of your most insightful posts. It really hit home right now.
    Thank you for sharing your wisdom, your thought process and even your journalling through decision making.
    I look forward to reading more of your writing soon.

    Like

  46. Any reason why my previous comment hasn’t been published? I’ve only said that sometimes I have a different approach to Tim’s.
    You say “Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff.” My comment was slightly critical (I hope everyone is entitled to an opinion), definitely not rude.

    Like

    • yeah, it’s inscrutable – I’ve left incredibly positive comments that got deleted. I can’t see the rhyme or reason either, FWIW (assuming this comment gets published, ha!)

      Like

      • I know, it’s a bit strange. I had only expressed my thoughts on self-help, saying that sometimes it’s ok to be just who one is. And I referred to a book called Zorba the greek. If they end up publishing it, you’ll see there is no rudeness whatsoever. What can I say…

        Like

  47. Glad to see this Tim. I recently sold, gave away and gave up everything tying me to my old way of life. From my home and toys to my work and income (fee for service- advising and coaching), all activities are now vetted by and subject to, my ability to apply my super power and create a life I truly believe in. If it’s not a direct fit I say no.

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  48. Brilliant!!!! Truly my favorit post thus far. With that stated,I am always gratefully educated by all of you teachings/writings/ideas. These post are my cup of coffee; thank you.

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  49. Tim

    I admire your courage to say No and have the wisdom to pursue your passion. Your Lyme disease symptoms will improve and may completely go away. This has been my clinical observation with people who are pursuing their life’s purpose.

    Dr. J

    Like

  50. THE BEST BLOG POST / EMAIL YOU HAVE EVER PRODUCED! You made me think about my own investments in people, projects, and in what I feel is obligatory; Obligatory = hell no, but I will do it any way. Thank you.

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  51. Wow Tim thank you for an incredible read and congrats on making such a ballsy move. You are making such an authentic and honest decision for yourself. It is so easy to slip in to doing something just because it feels “stupid” to do otherwise but I’m becoming a great fan of saying “fuck it” and just doing what the hell I want. Currently exiting my biz after reading 4hww 6 months ago … My current biz bores me to tears, fills me full of anxiety and is not what I was put on this planet to do. Thank you for changing my life I am now about to enjoy a mini retirement with 5 months of snowboarding around the world!

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  52. Thank you, I needed this.

    My one reservation is about the applicability of this for everyone. You could probably retire now and be fine for years, but what about those who don’t have that insurance? Is it reckless for some people to turn down opportunities? For example, what if you can’t afford to put health above client calls even though you need to? Is there a threshold for when you get to say no?

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  53. Hi Tim

    You’re not alone, as a Doctor this is exactly what I’ve dedicated with success, my life to. I’m not sure how else to share with you my project ( that requires no investing 😉) The Overwhelm Solution (.com)
    Daily I work with high profile , successful people that have hit the breaking point in their physiology, which over time effects their greatest asset , their minds. Joy starts to leak out, relationships deflate, and drastic changes are made that may not be necessary.
    My heart goes out to you, and I truly hope you find those precious sparks that ignite your soul fire into sustainable flames.

    Like

  54. In case it’s not Tim who screens these, please pass on The Overwhelm Solution, so he knows his genius is not alone , you don’t have to publish either post, no investing required, but as an advocate for lifestyle, and a man taking a stance for his health, him and so many of his followers could truly benefit from support like this.
    Thank you
    Dr Denoon

    Like

  55. Thank you Tim. I just discovered you and your thinking a couple of months ago. Although you say you are not the best writer, I have found that you are very clear. You are an excellent teacher and very inspiring. I feel that your latest decision as a wise one. I hope you enjoy your newest mini retirement and I am looking forward to your discoveries from it.
    Sara

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  56. Tim – as a consumer of your content (books/podcast/posts/etc), this article got me feeling “HELL YEAH!”. 4HWW changed my life, and in this article you dig into things that make me feel like back when I first read it. Thank you, and I look forward to what content you will put out there here on in with this renewed dedication 🙂

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  57. Tim, I believe the real challenge is finding our own authentic value in this life. When we tip the scale to our vocation to provide that worth we are chained to a false value that can flutter on at any moment. Rising in the ranks and gaining power provides a great sense of worth, but when that changes, and it will, and you have owned that success as your sole value, the dive down will be brutal. I believe you have discovered a search for authentic value; who is Tim as a soul in this life, not who is Tim and his vocation.

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  58. I left the safety and security of a high paying job to pursue my true passion. I’m struggling and am far from successful, and i’m terrified every other day..but then again, on the days in between I’m saying “fu** yeah!!” because I refuse to die with my song still inside me.

    I’m disheartened by the overabundance of folks who buy into the, “I’m too busy…” bs. Don’t they get it? Life travels at the speed of light.

    The fact you’re saying “no” at this point in your life sends a super wonderful message of empowerment. thank you.

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  59. I concur that this article is one your best. While I was reading it, the thought of an older (and wiser) mentor I had reminded me of her advice – “When life gets cluttered, it’s time to do some cleaning.”. Every year, I go through what’s working a d what’s not…similar to your process. And every year I write a letter to my future self with those decisions…and I find that the worst not only didn’t happen, I ended up making better life quality decisions.

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  60. The most profound post you’ve written. I applaud your insight and take it to heart. Our experience here on earth is not about aquiring…it takes huge courage, tenacity, grit and wisdom to learn that and let go and then do it again tomorrow, and the next until we’re 90 and surrounded by people and experiences we love, then we’ll know it was worth it. I’m inspired again, thanks Tim.

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  61. Thanks Tim for sharing this!

    It is important to be optomistic in life but it is also important to share moment that are harder… Thank you for sharing avoir your lyme desease and Fomo.

    I am a big fan of your books and blog and I am glad you are not going full time into VC as your writing have always made a big impact in my life.

    I have started to be a minimalist and enjoy having less instead of more and I still have a hard time adjusting this with my passions, personal projects and professional life but I believe it is a great lesson to learn to say no.

    Thanks again for this great post. Can’t wait to see how you stick with this and have more time to feel free and be even more creative.

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  62. Tim – I’ve read this twice now and it is so directly applicable to my life and actionable – one of the best things you’ve ever put out there, IMO.

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  63. Tim – your thought process and execution around decision making is world class and I am so thankful to you for sharing it with us. Thank you. I’m excited to see what you produce as you follow this path. I’m also going to use much of this post as I struggle to decide whether to take a fancy job title at a cool startup or continue to follow my dream and start my own company.

    More than anything I kept reading this and thinking, “so is this Tim’s way of announcing he’s going to write The 4 Hour Investor?”

    Sure seems like a way you can transfer the lessons you’ve learned in investing to millions of people. 🙂

    I’ll remain hopeful!

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  64. I felt compelled to write you as I had my breakdown/breakthrough back in June of this year. Waking up at 3am every day, wanting to puke, and asking the questions “Is this all there is?” and “What the hell am I doing this for?”. So I quit my job, took 2 months off with my kids for summer, and decided it was now or never to start a business. Even though I have no clients, I know – Everything Is as it Should Be. Worst case scenario – I go and find a job. I have always described my perfect day as being able to drop my kids off, work from home and pick my kids up from school. 2 out of 3 isn’t so bad. At the end of the day, if you’re dead, money isn’t going to matter one damn bit. Keep on keepin’ on.

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  65. I found myself bound to your podcasts. I spent time trying to read every book and research every guest before the next one came out.
    After going back and listening to half of them (@ 1.5 speed to save time) and reading the books recommended (using the speed reading techniques) I still had no time to do, to create, to make any of those things happen.

    So I am gonna take a vacation from your Podcasts. From everyones podcasts and blogs.

    I am gonna create.

    Thanks for giving us the tools to make things happen.

    Aloha!

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  66. Tim, this was the best post I’ve read from you! Thank you for being vulnerable and honest. This was just what I needed to hear as my life had become nothing but overwhelm. Though I’m female and not an investor (in other companies or start-ups), it was as though I was reading a page from my life while reading this blog post. I have been noting the same patterns in my life when it comes to taking on projects and opportunities that seemingly will brings me towards building the lifestyle business I am now creating. In reality, I’m in constant state of overwealm and stress, my sleep and personal health flying down the tubes…working so much so I can cover the cost of this and that in hopes of creating. I noticed in handling such business I have no time to actually do or create the very things I am trying market. CRAZY!!! Two days before reading this article I said NO to an opportunity that I initially said yes to. My heart was pounding and my breathing was restricted. Once I said NO relief…I am now considering the other things I have said yes to because I’m thinking a few of those will now be a NO. Thanks for this timely and life changing article.

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  67. Excellent post. I was thinking of doing the same. But…

    You said:
    “Some of you might suggest hedging with short positions, and I’d love to, but it’s not my forte. If you have ideas for doing so without huge exposure or getting into legal gray areas, please let me know in the comments.”

    You can short stocks with defined risk by selling vertical call spreads at one standard deviation above the stock price with a 67% expected chance of making money. Spread out over lots of stocks which you think are over-priced, you are statistically guaranteed to make money when placed on stocks with high implied volatility.

    This is not a gray area; it is 100% legal. People like Tom Sosnoff teach these kinds of trades daily. I do these types of transactions on a regular basis and the best part about them is ‘Defined Risk’ which helps me to sleep better.

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  68. Hey Tim,

    Just like to say that I’m looking forward to your upcoming work. I’ve always enjoyed your writing and happy you’re bringing it back. You’re one of the few writers that gives me deep inspiration. Welcome back!

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  69. Like they all said: GREAT post. Really well considered and referenced. My favorite quote: Life favors the specific ask and punishes the vague wish. Just like Scott Adams related with his visualizations in your podcast with him. All my experience tells me this, yet still it seems like human nature to be distracted with vague wishes of doing way more. Thanks for the encouragement to keep working at “no”.

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  70. Good to have you back, Tim!
    I’m way out of your demographic (female, early 60s), but your writing/teaching has changed everything about how I look at life and what I want to do with my last precious decades. Life is short! No guarantees, so you gotta go for it.

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  71. I am very proud of you for taking, possibly, a very challenge step! Slowing down and ‘missing out’ can be VERY frighting – at first! (Being there done that!)
    I enjoy A LOT your content and your ability to explore so many subjects and areas, and I learn A LOT from it! And … I had sensed a lot of anxiety in your process and talks lately, and I was, actually, sending some good vibes for you to consider the ‘slow down’ possibly. My selfish intention was having you health and able to continue to provide, with clarity, the great service and information you provide. I am glad you are taking this important challenge
    Slow down happy vibes! Hand on in this the process! It is worth!
    Less is more!

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  72. Hi Tim, your honesty and commitment with your principles are admirable. I need to confess that for a while I felt you seemed distant from your beliefs, working like crazy in new projects and saying yes for everything that looks cool. However, the mathematics don’t close: staying beasier isn’t a guarantee of success; have rushing in the morning or pulling from one meet to another don’t make sense in the long term. Glad and inspired to hear you are backing to the simpler, the real , the less that is more. I wish you all the best. Keep inspiring people! KR

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  73. Great article Tim. I’m an avid follower of your content from your books to your podcast and TV show. Kudos to you for recognizing when to stop doing something you no longer share the same enthusiasm for and realize it’s affecting other areas of your life. I think fulfillment rather than success is most important, as the intrinsic value of how your time and focus is spent means everything. I look forward to seeing what you put out next, as I agree with many others in that you are an exceptional teacher and have much to share with the world.

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  74. Superb article Tim, just what I needed right now. As soon as I started reading your post I immediately thought of the guy you referenced, Greg McKeown’s Essentialism. I need to get back into this thought process. I also agree with some of the other posts, this has been your best for a while. Get rid of the many good and concentrate on the vital few.

    Today I reposted an image from Richard Branson which said:

    If you want happiness for an hour – Take a nap
    If you want happiness for a day – Go fishing
    If you want happiness for a year – Inherit a fortune
    If you want happiness for a lifetime – Help someone else

    This is what you do best when you write Tim.

    Cheers, Andy

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  75. Just wanted to say thanks! I am working (albeit slowly) towards my personal FREEDOM. We can become slaves to what we think we master. Your posts and podcasts always stir my brain to think and my body to take action. Thanks again

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  76. Well done Tim!!!
    your decision doesn’t surprise me, kind of ….had the feeling your life was getting too complicated and being back to base could be good….for a while in your case.
    You saw it coming and took action….as you always do. Brave!
    Enjoy and don’t disappear for ever….you are a great inspiration…..
    Gracias por tantas enseñanzas y buenos ratos

    CRIS

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  77. Congrats! It was clear during the podcast with Tara Brach that this was what you needed to do but you were still talking yourself through it.
    I recently experienced a similar situation. I’ve planned for the past 2.5 year plan to quit my job and travel but got promoted twice in the meantime. I knew that waiting for my bonus in 5 months was the decision that looked best on paper but it didn’t feel right. A close friend finally gave me the answer I wanted to hear and now I’m in Tokyo, the first of many places I’ll be visiting for an undetermined amount of time.
    This isn’t the first time I’ve left my job to travel but your writings have been a great source of inspiration and support over the past few years as I’ve faced pressure from friends, family and cohorts not to not make the leap as well as my own FOMO.
    Glad you’ve hit the reset button. What you’re best at is probably what’s easiest and will make you happiest.

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  78. Thanks for the reminder to re-evaluate Tim. I by no means have it all, but I work from home now making a comfortable 4-600k per year and I mostly enjoy what I do. To be honest though I did re-evaluate what causes me stress and takes up more of my time than I want. I keep finding my fear to change comes from the very basic worry that I could lose it all. Every time I do fear setting exercises I realize that even if I did lose it all its not something that I couldn’t just rebuild and probably enjoy doing. Thanks for the encouragement and personal insight.

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  79. Hi Tim, Long time reader and follow your podcasts at the gym. Love the quote by Yutang about eliminating non-essentials. I do consider you a teacher first and glad to see you know yourself well enough to take a break from some of the non-essentials. Looking forward to your insights as you scale back. PS. The article about you in Success magazine was wonderful.

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  80. Tim: I believe a good hedge shown over time is a systematic trend following algorithmic trading system, via Liquid Futures. It is a way to control risk in the least non correlated fashion. Although long term in nature I believe it is the most robust. It is also a quantifiable method which works and to me takes the angst out of less systemized and more correlated methods.
    Thanks Matt

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  81. Tim, thank you for this awesome post- one of your best without a doubt.
    I am very grateful to you for your insights and for your writing. I did a 180 on my life immediately after reading 4HWW, and learnt a ton from 4HBody too.
    I am clearly just one of many influenced by your insights. This post is wonderful because you have reached a new level of awareness of self. You have always been super smart, witty etc and now you are becoming super wise as well. So freaking awesome. Super, super happy for you. Thanks again for your wonderful insights. Big love and gratitude

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