Quitting Time
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Audio Recording by George Hahn
Few virtues are more celebrated in America than perseverance and grit. Commencement speakers offer a similar battle cry: “Never give up!” Jesus, what bullshit. Entrepreneurs aren’t voted into the hall of fame unless they have a story about mortgaging their house to make payroll or cleaning the first apartments rented on the platform. Sir James Dyson made 5,126 prototypes of his bagless vacuum cleaner, only to be rejected by every manufacturer in the U.K. Jack Ma was rejected by Harvard 10 times. Grit is great. Perseverance is a virtue. But, narratively, it’s overrated. Greatness is a function not just of grit, but of talent, luck, where and when you are born … and knowing when to quit.
Rebrand
Don’t quit, “reboot.” Quitting is “onwarding.” The point is that similar to not-quitting, quitting is also a virtue. In fact, it’s a necessity. The most successful prehistoric peoples were willing to leave a place when they observed a decline in prey or a change in the weather. Most CEOs have one thing in common: They are quitters. Specifically, your career trajectory will be steeper if every several years you switch jobs. Strangers, from a distance, find you more attractive than co-workers, who can’t help but look at you through the lens of when you joined the firm. Our Editor in Chief at Prof G is an übertalented young man straight out of Yale who needs guardrails. Except he isn’t, he’s (now) a 51-year-old seasoned exec with several master’s degrees. (We’ve been working together for 27 years.)
Nothing Ventured
Anything that offers substantial rewards comes with risk, a high likelihood of failure. Which means you’ll need to make several appearances at the plate before you connect with the ball. The top scorers in the Premier League miss half their shots. Great players, like great entrepreneurs and leaders, see the ball go wide, shake their head, and move on. If you want to be successful, you will likely need to quit the majority of your jobs, homes, friends, and investments. Your jobs, locale, investments, and relationships are commitments, not suicide pacts.
What get labeled ”overnight successes” rarely are, and the best way to become an overnight success is to work your ass off for 30 years. Most hugely successful entrepreneurs don’t hit it on their first venture. Mine was pushing a Rubbermaid service cart full of VHS tapes for rent to law firms and ad agencies in L.A.’s Century City. Ever see Cousins or Turner & Hooch and work in the Century Plaza Towers in 1989? If yes, we’ve met before. I quit when my inventory of 1,100 tapes was stolen from my Mom’s garage. A better frame/narrative: I “onwarded” my firm (“StressBusters Video”). It was acquired when I discovered my mother had homeowner’s insurance.
Grit
A big data study of 46 years of VC investments found prior failure to be “the essential prerequisite for success.” The key is learning from each mistake. Startups have a 1 in 10 chance of success. That sounds intimidating. But really it’s exciting, because if you have the emotional resilience to start seven companies, you’re likely to be the founder of a successful firm.
I’ve started nine businesses, and most didn’t work. But they all taught me something. My biggest professional failure was Red Envelope. Yes, we were backed by Sequoia Capital, Chanel, and Weston Presidio, and went public. But due to all that “success,” I didn’t quit soon enough — it took more than a decade to fail. Brand Farm, an e-commerce incubator, was much less successful than Red Envelope. It was a bigger success for me, though, as it started and ended in just nine months. I closed the Series A in November of 1999 (i.e., bad timing), saw the writing on the wall soon after, and shut it down. In 2010 I founded business intelligence firm L2, bootstrapped it at first, then sold it in 2017 for $158 million, 27 months after our first and only round of financing.
If success is the best thing, failing/quitting fast is the next best thing. Also, keep in mind that the market is bigger than any individual, and most of your success/failure is not your fault. Be humble when things work and willing to forgive yourself when they don’t. Again, I’m not disputing the importance of perseverance. Quitting isn’t the opposite of persevering, it’s the raw material. Dyson’s 5,126 failed prototypes were only possible because after each one, he shrugged, learned what he could, and put it aside to try again. That’s 5,126 little quits.
The Myth
We have a mythology where the hero never gives up. “Come back with your shield, or on it,” Spartan mothers told their sons. This attitude gets us in trouble, as people caught flailing have a map that only depicts one thing and one direction, the higher ground directly in front of them.
Elizabeth Holmes famously said there was “no plan B.” Well, turns out there was a plan C, as she couldn’t fathom B. Plan B was a bright future after starting a firm with a bold vision. Sadly, her prototype, like those of several hundred other tech firms, didn’t work out. In America, we’d rather you go to jail than come home without your shield. I’ve seen marriages fall apart under the stress of one partner chasing an unrealistic dream, and companies go under, unable to pay employees, suppliers, or the federal government (e.g., payroll taxes).
When to Walk Away
The challenge is knowing which part of the script you’re in. Are you at the moment where, if you dig in, your perseverance will pay off? Or are you somewhere in the first 100 minutes of the movie, experiencing just one of a string of failures? Math offers a hint: You’re likely to experience many more failures than successes, so if you know nothing else about your situation, be open to the notion (gasp) that this may be one of the failures. And, most important, that you and humanity will survive it.
Quitting often requires walking away from years of invested time and capital. Our brains aren’t wired for this — we’re unable to recognize that sunk costs are … sunk. One study asked participants to imagine they had bought nonrefundable tickets for two different weekend trips, one costing $100, the other $50, but they’d inadvertently bought them for the same date. The $50 trip would be more fun, they were told. Which trip would they take? Irrationally, 54% of people said they would go on the $100 trip. We hate walking away from an investment.
Semi-quitting (i.e., diversifying) is a critical skill in good times, as well. On the boards of startups, at every subsequent round of financing, I encourage management and employees to take some money off the table. And, increasingly, this is an option for small growth firms. It’s amazing how the power pendulum has swung from VCs to founders. When I was starting companies in the nineties, VCs and bankers wouldn’t tolerate this. “That would send the wrong signal — aren’t you in this to win?” Pro tip: If you have 80+% of your net worth in one asset and people try to stop you from diversifying, they do not have your best interests at heart.
The Alchemy of Success
It’s a useful exercise to assess the underpinnings of any success you’ve enjoyed. For me, it’s been three things: 1) Being born in America in the 1960s. The University of California, Pell grants, the microprocessor, capitalism, and a tolerance for failure. 2) My mother’s irrational passion for my well-being. Despite struggling with depression and anger, I’ve always been confident. I believe this is a function of an impressive person telling me every day, in a thousand ways, that I was wonderful. And 3) I inherited the “leaver” gene from my immigrant parents.
My dad left Glasgow and a household of violence and alcoholism. My mother left London when her two young sisters were still in the Jewish Orphanage in London. Among my close friends from college, I am not the most talented, and we all had similar credentials. I’m one of the most successful (professionally), as I was the only one willing to leave L.A.: Investment banking in New York, starting tech firms in SF, teaching in NYC, entrepreneur (again) living in Florida, now media (best description I can come up with) and living in London.
These moves felt risky at the time, but they pale in comparison to the courage it took my mother to board a steamship headed to Toronto at 24, armed with an 8th-grade education and 200 quid. Five years later, married and 7 months pregnant, she left Toronto for San Diego. My parents’ robust analysis of where to move? A: They read in the newspaper that San Diego had the best weather in America.
High Counsel
I’m not suggesting you be reckless, get divorced, and head for Key West. Even Cersei Lannister had a High Counsel and a Hand (senior adviser). Spoiler alert: She stopped listening to them. Everyone needs their own High Counsel, and you should not make any big decision without the benefit of their input. It’s difficult to read the label from inside the bottle. However, the thing that often holds back people who are emotionally strong and talented is their hesitancy to leave, to quit. It’s a vastly underrated strength.
I just purchased tickets for the Carabao Cup. Tickets increased in price by 20% when Liverpool manager Jürgen Klopp announced he was leaving the club. Liverpool’s manager is quitting with his team in first place, and his stature enhanced, because he didn’t feel he had the energy he owed the team — and the fans love him for his integrity. That’s a form of strength.
Shame
Nobody is paying as much attention to your failures as you are, so fear them but don’t let them paralyze you. When you do fail, don’t feel you need to excuse them or blame others. Being gracious in victory is admirable. What’s harder, but can pay greater dividends, is being gracious in failure. Express gratitude to everyone who believed in you, and demonstrate grace to those who didn’t.
Shame and fear of embarrassment often hold people back from leaving … and leading a better life. Carl Sagan’s insight helps liberate me from that angst: “We are mites on a plum on a planet circling an unremarkable star on the outskirts of an ordinary galaxy which contains 400 billion other stars and is one of 100 billion other galaxies.” Nobody you care about or who cares about you will be alive in 100 years. Nobody will remember your successes or failures. To let fear devour your short time here is to not understand the most basic law of the universe: your insignificance. Why would any of us not enjoy ourselves and not love others with abandon?
Walking Each Other Home
There’s a wonderful line in the film Men Up. The lead character believes he knows the meaning of life: We’re all just walking each other home. On your way home (i.e., success, reward, love) the key is not knowing or sticking to any one path — at 18 I was certain I was going to be a pediatrician living in Santa Monica — but investing in relationships so you’ll know, no matter the route, there will be people walking with you.
Life is so rich,
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Grit and perseverance are the hallmark of Palestinian resistance you seem to completely disregard and belittle in your previous pieces. Resisting occupation and apartheid do not mean the annihilation of Israel, they mean giving indigenous people the dignity to live free of oppression by resisting occupation and apartheid. Many of us expected so much more of you Scott.
Great blog. Totally agree. Our small business is now crushing it, wasn’t our first try and it took 5 years. But, most liberals will tell you “Grit” is racist as DEI rewards your race/gender NOT Grit. Seriously, liberals consider Grit and Achievement racist.
Definitely one of the best essays I have read recently – honest, authentic and somewhat moving at the same time
Thank you for this. It was exactly what I needed to hear at exactly the right time.
Thank you for this.
“We’re all just walking each other home” is a famous line from taken from Ram Dass. Even more to your point, the idea is that everything we do and everyone some does for us is reciprocal in nature. While my mother was passing away I was helping her her to “walk home” and in turn, she taught me what passing away looks like, how to teach my boys about death and helped my “walk home.”
Excellent advice Prof.
Most people struggle with their egos instead of focusing on learning from the experience and “rebooting”. Agree with you about Klopp – his stature has indeed increased.
Just one thing – disappointed with sentence 3 of your blog. Very unnecessary to use such language.
Some sage personal ‘story’ of emergence, growth here. The success ‘alchemy’ or situation is ace. We all take too much credit for our ‘own’ success, when we’re walking each other home, on the shoulders of giants. So to speak!
Is this a play on “Winning Time” – the HBO series on Lakers early days. In any case, both are fun and interesting – that series and this essay!
I think Ego is what holds most people from leaving.
With the help of your friend Richard Reeves I wrote a piece for Brookings in 2018 on military service being the last vehicle of American social mobility – trading autonomy for healthcare, housing allowance, vocational training, and the GI Bill transferred to your kids. As you’d say Scott, the Champagne and Cocaine of generational wealth!
What your piece has me thinking of is the additional benefit of public service in your 20s as an “alchemy of success.” I served for 22 years flying jets off aircraft carriers, doing research in a think tank, and advising at the White House. I was never in the same “job” for more than a year and a half. I moved on average to a new city every three. I failed more often than I’m proud of but just enough to keep learning through the finish line. Public service (State Dept, Teach for America, Peace Corps, Naval Aviation) is both a social mobility and career rocket ship. We just don’t make successfully make the case. Would love to hear you and Ed talk about these topics. Ping me with any questions! Keep up the great work.
After last week’s disaster…Scott’s back! Good stuff!
100% –> “The thing that often holds back people who are emotionally strong and talented is their hesitancy to leave, to quit. It’s a vastly underrated strength.”
Scott, I did not see the word “pivot” anywhere in this episode, but I think what you are advocating includes pivoting as a way of intelligently quitting in order to keep advancing, whatever effort that may pertain to. Lots of important lessons and takeaways in this article. Thanks for the enlightenment!
Needed these insights today! Thank you, Scott!
Loved your post today. I listen to your podcast religiously. I am sending this to my adult daughter who is very talented but stuck in a job she does not like. This is shaking her self confidence and is getting depressed. I was raised not to quit but stay in a job. I wish I knew this when I was younger. Thank you for your wisdom.
The most basic law of the universe may not be our insignificance, but rather, how do we reconcile that sense of insignificance while also knowing that, if only by our mere presence on this planet, we each will uniquely and eternally alter the entire course of human history.
Perfect timing. I’m a couple years into launching an educational non-profit. At the beginning, I told my board and supporters, “It’s gonna be like X, Y, Z.” Now that we’re in the sales cycle, it’s completely different. I have felt this compulsion to stick to what I said originally, even though I now know that it was said in ignorance of actual selling conditions. Your piece helps me see that I not only need to adapt, I need to do so with confidence and even a bit of boldness until… the next time I need to adapt again!
A very nice article. What if your relatives do not support you? What to do then?
Scott, when does a personal. Know to quit??
Goddammit why aren’t you running for POTUS…???
Great article! Helped me a lot
Simply wonderful this essay.
Nice to read this. In My first full time venture, I lost so much money and time but was too proud to quit. Just too much grit and too much of perseverance. as tightly mentioned in the post, not enough to make it. Needed a high counsel or hand to tell me to quit .. hopefully I would have quit listening to them . But then again, I was so hard headed that I might have not listened to them as well. Sometimes only pain teaches some folks. I felt the pain and learnt.. can’t be too proud of that but it set my foundation moving forward. In hindsight, wish I would have quit way earlier ..
Good comment. I have made four fortunes and lost three. The last being my invention of Internet TV with my company Viewcall America which was kyboshed by Oracle and Acorn an English company who broke confidence and claimed it for themselves and bust Viewcall.
Wonderful piece.
Great post!
Never give up sounds great, and makes great plot in movies. Key is to know when to walk away.
Most people are just trying to get though the day and hoping to get it right. What you describe is almost a luxury. Please write about Ozempic. On Bill Maher’s show I remember that you said this medication will have more impact on society than AI. I agree, but then I predicted the obesity epidemic in 1978. And I think thatTrump has benefited from 65% of the population who are obese and self-shame.
Spot on, I’m quitting my current company, and starting another that builds on what’s working and the AI + Gen AI tech now available. I should have quit years ago; I was afraid and felt ashamed. I wish I had seen this newsletter a few years back. Great one!
I always love when I see you in my inbox. You make me smarter. In this piece, I take umbrage with one nuanced thing. Quitting does not equal failing. Failing and its sister, getting back up are necessary antidotes to hubris. Quitting a boring job with a high paycheck is necessary for sanity.
Great post
Your on fire Scott – excellent written piece. Thank you for sharing
Thanks for writing this. The timing is perfect for what is transpiring in my life and motivational.
Like you, I have been around the block and these times are changing rapidly.
Been fortunate to have had the bulls and been bitten by a few snakes but our failures are just as important as the triumphs. Life is not as easy as a tik tok video and perseverance needs to be taught across all aspects of our lives. Surround yourselves with those who dare and love your failures just as much as your successes. Sadness and or depression is just you gathering strength for the next push. All tidal waves have a crests and throughs.
54% is interesting but not meaningful. For a good look into shame, read Start-Up Nation. Look at the contrasts between Israel and its Arab neighbors. In Israel, they are Japan-like, as in falling down seven times and getting up eight. The society encourages risk-taking. In Arab culture, there is a huge shame element. I don’t know if that’s cultural or religious. Compare the innovation and number of patent applications coming out of an eight million population, diverse country with the dozens of countries with mostly Sunni Arab countries in the neighborhood. Maybe it’s service in the military, where nineteen-year-olds make life-and-death decisions on the fly instead of getting wasted for four years right out of high school in the US. Compare that to the rigid Soviet doctrine in Arab armies. In 2021, the World Bank shows that Israel applied for 1,521 patents. Jordan 21. Iraq 635, Kuwait 1 (!), Egypt 881 (10x population). Don’t @ me.
Thanks for the WAKE UP.!! I was drifting to far from the shore. I remembered that I went out on the road to find out where it was At & found out the road was where it was At.
An excellent post ..!! The lyrics to the Kenny Rogers song, sums it up:
“You’ve got to know when to hold ’em
Know when to fold ’em
Know when to walk away
And know when to run
You never count your money
When you’re sittin’ at the table
There’ll be time enough for countin’
When the dealin’s done.”
Too many edibles………again
The truth. As a longtime entrepreneur I’ve generally known that the odds were stacked against our ventures. However, over time the tough experiences and hard won successes have yielded so many valuable things. Be as objective as you can be, listen more than talk, don’t procrastinate, be adaptive, move more than sit, and enjoy the journey because it’s uniquely you.
Don’t think grit is an Aristotelian virtue
Great post and shows why we need more Merit, Grit, Hard Work and far less DEI nonsense and less government in our way!