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How We Secretly Lose Control of Our Startups
Should Kids Follow in Our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Stop Listening to Investors
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
What Is Startup Funding?
Do Founders Deserve Their Profit?
Michelle Glauser on Diversity and Inclusion
The Utter STUPIDITY of "Risking it All"
Committees Are Where Progress Goes to Die
More Money (Really Means) More Problems
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
Do People Really Want Me to Succeed?
Is the Problem the Player or the Coach?
Will Investors Bail Me Out?
The Value of Actually Getting Paid
Why do Founders Suck at Asking for Help?
Wait a Minute before Giving Away Equity
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
The 9 Best Growth Agencies for Startups
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
Never Share Your Net Worth
A Steady Hand in the Middle of the Storm
Risk it All vs Steady Paycheck
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset
My Competitor Got Funded — Am I Screwed?
The Hidden Treasure of Failed Startups
If It Makes Money, It Makes Sense
Why do VCs Keep Giving Failed Founders Money?
$10K Per Month isn't Just Revenue — It's Life Support
The Ridiculous Spectrum of Investor Feedback
Startup CEOs Aren't Really CEOs
Series A, B, C, D, and E Funding: How It Works
Best Pitch Decks Ever: The Most Successful Fundraising Pitches You Need to Know
When to Raise Funds
Why Aren't Investors Responding to Me?
Should I Regret Not Raising Capital?
Unemployment Cases — Why I LOOOOOVE To Win Them So Much.
How Much to Pay Yourself
Heat-Seeking Missile: WePay’s Journey to Product-Market Fit — Interview with Rich Aberman, Co-Founder of Wepay
The R&D technique for startups: Rip off & Duplicate
Why Some Startups Win.
Chapter #1: First Steps To Validate Your Business Idea
Product Users, Not Ideas, Will Determine Your Startup’s Fate
Drop Your Free Tier
Your Advisors Are Probably Wrong
Growth Isn't Always Good
How to Shut Down Gracefully
How Does My Startup Get Acquired?
Can Entrepreneurship Be Taught?
How to Pick the Wrong Co-Founder
Staying Small While Going Big
Investors are NOT on Our Side of the Table
Who am I Really Competing Against?
Why Can't Founders Replace Themselves?
Actually, We Have Plenty of Time
Quitting vs Letting Go
How Startups Actually Get Bought
What if I'm Building the Wrong Product?
Are Founders Driven by Fear or Greed?
Why I'm Either Working or Feeling Guilty
Startup Financial Assumptions
Why Every Kid Should be a Startup Founder
We Only Have to be Right Once
If a Startup Sinks, Founders Go Down With it
Founder Success: We Need a Strict Definition of Personal Success
Is Quiet Quitting a Problem at Startup Companies?
Founder Exits are Hard Work and Good Fortune, Not "Good Luck"
Finalizing Startup Projections
All Founders are Beloved In Good Times
Our Startup Culture of Entitlement
The Bullshit Case for Raising Capital
How do We Manage Our Founder Flaws?
What If my plan for retirement is "never retire"?
Startup Failure is just One Chapter in Founder Life
6 Similarities between Startup Founders and Pro Athletes
All Founders Make Bad Decisions — and That's OK
Startup Board Negotiations: How do I tell the board I need a new deal?
Founder Sacrifice — At What Point Have I Gone Too Far?
Youth Entrepreneurship: Can Middle Schoolers be Founders?
Living the Founder Legend Isn't so Fun
Why Do VC Funded Startups Love "Fake Growth?"
How Should I Share My Wealth with Family?
How Many Deaths Can a Startup Survive?
This is Probably Your Last Success
Why Do We Still Have Full-Time Employees?
The Case Against Full Transparency
Should I Feel Guilty for Failing?
Always Take Money off the Table

Why I'm Either Working or Feeling Guilty

Wil Schroter

Why I'm Either Working or Feeling Guilty

I have two modes — working all the time and feeling guilty about not working all the time. There's no third mode.

I'd love to say this is a new phenomenon or that I've got some monopoly on this curse, but having spoken to countless Founders just like me, it appears I'm certainly not alone.

Now, part of that might just be self-selection. Perhaps the people who tend to work tirelessly often want to do it for themselves, or at the very least, have more motivation than the people they left back in their cubicle farm. I can't think of anyone who works harder than a Founder without anyone telling them to do it!

How Did This All Start?

Everyone's origin story comes from somewhere else, so I can't pretend to triangulate the genesis of this affliction from one single source. Mine happened to that be I grew up a ridiculously poor kid whose parents abandoned him and had to do whatever he could to escape that. Hopefully, yours was much less painful, but it probably wasn't.

So as a kid, I would quickly tie working hard and hustling to "safety and survival". I didn't have lunch money, so I would have to go run a little candy sales ring in 7th grade to come up with the funds. I didn't have a way to pay for college, so I would have to work two 40-hour jobs per week and go to school full-time on the weekend.

Everything was always solved with a single option — work more. But that work gave me the fundamental safety I needed to survive. If I'm being honest, it was awesome! I never minded working harder, and to me there's nothing more genuine than earning your keep. It's definitely what made being a Founder so appealing to me.

It Went Great... for a While

When I was 19, I started my first company, and all of a sudden, my work-all-the-time mantra was given a proper outlet. As Founders, working all the time is kind of the job, but for a guy like me who loved working, it was heaven. The years from 19 to 25 were mostly a blur. I don't remember anything about being in college, only that I worked the whole time. Most people have college memories of their first keg parties. My memories were the first enterprise deal I closed.

My work ethic and ambition were rewarded handsomely. The company grew by leaps and bounds, and the more I worked, the more I achieved. It was glorious, and for the first time in my life, I was being rewarded not just with enough to pay for food but enough to build a savings account. From that point on, I could easily attach "more safety" to "more work."

When you're rewarded for behavior, you're naturally encouraged to do more of it. The problem with a reward cycle is that there is rarely ever any indication that the cycle has been broken.

And Then it Became a Curse

So what happens when all the work gets you the things you want? You stop, right? Do you sit back and enjoy it? Nope. Not even close. You get to a point where you are so hard-wired over such a long period of time to associate "work" with "safety" that the idea of not working feels terrifying.

I get up at 4 a.m. (I don't recommend it) and start working. I will keep working, sitting at my computer non-stop, sometimes without breaks, until my wife literally pulls me out of my office. When I take breaks — I feel guilty. When I take a vacation — I feel guilty. The only time I'm not guilty is when I'm working, which obviously sounds awful because it is.

I share this little cautionary tale not as a personal cry for help (I'm good, mostly) but as a reflection for my fellow Founders. Whether you're just starting your career and you haven't yet realized what this extreme mindset can become, or you're well into this affliction and you're reading this saying, "Wow, this is a problem."

The work is important, but it's also a means to an end, not an end itself. Unless we find a way to enjoy the fruits of our labor, then, well, it's just labor. And that doesn't sound like any kind of fun at all.

In Case You Missed It

Why No One Tells Founders "It's over, move on." (podcast) No one ever actually tells Founders it’s okay to quit. No one except other Founders, of course.

How Do I Design My Startup Around My Life? There’s very little preventing us from designing our startups around our life goals. It starts with us being very clear about what we want to achieve and then taking clear, small steps toward those outcomes.

The Curse of the 37-Year-Old Founder Let's talk about the dues Founders pay for neglecting their health. Pushing yourself too much, putting your body through so much pressure, and then ignoring the warning signs as they come, you’re unconsciously trading your life for the success of your company.

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Miakosl Lians

Putting undue stress on your body by overtraining and failing to recognize the warning signals

Reply8 months ago

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