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Does Startup Success Validate Us Personally?
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
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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?
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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?
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This is Probably Your Last Success
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The Case Against Full Transparency
Should I Feel Guilty for Failing?

7 Lifestyle Choices of a Successful Entrepreneur

Carmen Sample

7 Lifestyle Choices of a Successful Entrepreneur

1. You will never take a “real” vacation again.

Lifestyle Choices

I am 7 years in and I have come to accept that it is not possible for me to take a “movie vacation” — ya know on a beachfront bungalow with no internet connection, remote from the working world…. And let’s be real — to an entrepreneur that simply doesn’t actually sound fun or relaxing at all. My ideal lifestyle is to be semi-connected on vacation. I’m a phone call/text message away and I will choose when to respond to emails. That may be the extent of my ability to fully “vacation”…and I’m honestly ok with that. Just as I sleep better when my kids are under my roof, I also sleep better when I’m accessible to my business.

2. You will decrease your friendship pool.

Where do most people find their good friends as an adult? Work!!! You guessed it. When you are the boss, it is an ongoing challenge to find friends because you have to do it outside of work. Of course I still have great work relationships. Yes, we really like each other. Yes, we are friendly, but truth is — true best friends can’t fire each other. This one really sucks actually as the concept of “It’s lonely at the top” is a really true thing. It’s even harder when you hire people that you would like to be friends with. That said, the power differential is there and will always create a necessary barrier, even if you never have to use it.

3. You will talk about work more than anything else.

Yes, you will do it to the point of full annoyance to others. I think primarily about three things: My kids, my husband and my businesses. That is pretty much ALL I think about. I may not be able to hold an intelligent conversation about the conflict in the Middle East, but I can talk about business and work all night long….and I will if you let me.

4. You will lose and gain friendships over “work habits”.

I have a fairly high tolerance to talking about religion and politics and can maneuver those conversations generally well without a lot of conflict. That said, I can lose my cool pretty quickly when I have vastly differing work habits than my friends. My husband will remind people that “work is religion” to me, in an effort to warn people to be careful how they proceed in a conversation. It is true. If I see my friends start to do weird things in their places of employment I have a hard time being close friends with them. I identify with the bosses they talk shit about and I can’t help but judge them when they glorify “calling in sick” when everyone knows they weren’t really sick. It isn’t funny and work habits matter to me, because work habits are what define a large part of my world.

5. Your choice in a spouse/partner may be the most important choice you make.

Your partner has to simply understand AND SUPPORT that your business is like another child. It is your lifeline and if it calls, you need to go. Even more challenging, your partner has to not take that decision personally. My husband will see it in my eyes if I am worried about something and he will stop me and gently say “Do you need to go work?”. Well YES, I do — thank you for not making me feel guilty about it. xoxo. Do you have a partner that promotes any concept of “work shaming”? If so, I would really examine if choosing a business that will dominate your attention is a good idea.

6. Being alone will be your new norm.

Oftentimes, I find myself completely alone in my entrepreneur world. There is no one to consult with, no one to complain to and no one else that will every fully “get it”. I find it exciting to stretch myself to create my own path, though it can simultaneously be a bit scary and lonely. One of my favorite bedtime stories for my kids is Dr. Seuss’s “Oh the Places You’ll Go”. He speaks to this so well:

“All Alone! Whether you like it or not, Alone will be something you’ll be quite a lot.
And when you’re alone, there’s a very good chance
you’ll meet things that scare you right out of your pants.
There are some, down the road between hither and yon,
that can scare you so much you won’t want to go on.
But on you will go
though the weather be foul.
On you will go
though your enemies prowl.
On you will go
though the Hakken-Kraks howl.
Onward up many
a frightening creek,
though your arms may get sore
and your sneakers may leak.” — Dr. Seuss

7. Social media will become an avenue that is exclusively used for work.

It’s true. I try to engage in it from a perspective of connecting with others personally, but it irritates me…. The truth is, I probably wouldn’t have a single social media account if I wasn’t trying to promote my businesses on it in one way or another. I have a one-track mind and if I don’t see a way to ultimately make money with something I probably won’t engage in it.

I love the entrepreneur lifestyle — I breathe it all day every day. I even wrote this blog post while out of the country on a “Vacation”. It isn’t for everyone, but I support anyone that wants to try! I will be happy to talk about your work to an obsessive level and be your new best friend. Just find me on the social media accounts that only exist to promote my businesses.

“And will you succeed? Yes, you will indeed! 98 3/4 percent guaranteed.” — Dr. Seuss


Also worth reading:

  1. Entrepreneurial Fitness: Master class by Shawntae Spencer
  2. The Emotional Cost Of Being A Startup Founder
  3. The Emotionally Fit Founder, Part One
  4. The Reality of Working for a Startup | It Isn’t All Ping Pong Tables and Free Snacks

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