An Alternative Definition of Entrepreneurial Success

This article, as the others on this site, is a work in progress. It’ll evolve as my thinking on the subject does, as I read more, talk to more people, and experiment more.

It’s been hip for a while to go against the hustle culture, but usually, the people who advocate that are people who have already sold their businesses for fuck-you money, who are already very financially secure, and who have gotten to that position by working their asses off and, oftentimes, to the detriment of other areas of their lives, including their health.

That’s not what I’m interested in.

I’m interested in how we can live a fulfilling life while running our businesses, and without running ourselves to the ground.

While I’ve always tried to dedicate ample time to things outside of work, I didn’t use to do it in a sustainable way. I was ignoring the signs my body was giving me and continued to live without taking breaks. Work, self-development, exercises, dance, dating (which inevitably led to more self-development), building friendships in a new country, … I took no breaks. And it caught up with me.

Unfortunately, this life of non-stop productivity left me with nervous system dysregulation without the financial freedom some (let’s be honest: a few) others reach after several years of being self-employed.

All of this to say that I’m not the expert telling you how to build a successful business while leading a satisfying life and without burning out. I’m the person who has, from the start of her entrepreneurial journey, wanted to live a fulfilling life, failed at her first attempt, and is now pondering how to do better this time around.

I invite you to ponder along with me.

This exercise looks different for everyone, but for me, it starts with an alternative definition of entrepreneurial success. One that doesn’t determine success based on revenue and company size, but on founder’s fulfillment and the notion that life and work aren’t separate, but interwoven.

This is a good moment to tell you I’m a solopreneur. In my first business, I managed a team of several freelancers and while I sometimes still hire people to help with specific projects, I consciously keep things small. My thoughts on entrepreneurship and success are personal reflections, based on my own experience, conversations in the circles I move in, and the things I come across online. My writings here are by no means meant to be exhaustive guides.

Seeking Fulfillment Before Financial Freedom

Imagine 10 years from now, your time is up. You didn’t see it coming, but you find yourself on your deathbed with days, maybe only hours to go. You look back at your life and one of two scenarios has played out.

Scenario 1:
You’ve worked hard to build a successful business and over the last year, you’ve been able to take yourself out of the daily operations. While you’re still involved, you can now enjoy the high salary you pay yourself, and the time you’ve freed up.

However, you got to this point by focusing relentlessly on your company, maintaining only a few friendships, traveling mostly for work, and forgetting about all of the little things that used to bring you so much joy. You might be single, or in a relationship with a very patient someone who you haven’t gone on many adventures with. Or you might have just been tired for nine years in a row.

Scenario 2:
Your business is doing well enough. You’re not near being financially free, but you work a maximum of 20 hours a week and your income is pretty stable. You can afford all of the things you need as well as most of the things you like, but you prioritize what you spend on so you can still put money aside every month.

You have a strong community around you and spend a lot of your time with friends, on hobbies, and exploring your interests. While you don’t stay at 5-star hotels, you travel frequently for fun, maybe even with a partner you go on regular dates with.

Knowing that you don’t have any time left, which of those scenarios would you rather be in? Would you still have been happy to have spent nine years focused on growing your company when you’ve only had one year to enjoy “the rest of life” more?

I think there is a growing awareness in the entrepreneurial community of the importance of spirituality, play, health (not just fitness), and non-work relationships, but I also think the awareness of that importance oftentimes comes after one or the other “Oh fuck”-moment.

“Oh fuck, I’ve sold my business and now realize it was my whole life.”
“Oh fuck, I don’t know what to do with myself when I’m not working.”
“Oh fuck, I haven’t felt joy in ages. What now?”

I’m painting a bit of an extreme picture, but you get the gist.

This balance between building for the future and enjoying the now will look different for everyone, and it may look different for the same person at different moments in time.

But we don’t have to look at this as an “either, or” question. We can approach it from an “and” perspective.

An Alternative Definition of Entrepreneurial Success

Within the realms of entrepreneurship, “successful” is often defined in terms of how much revenue your business makes, how many customers or clients you have, how big your team is, how well-known you are as a founder or solopreneur, how big of an exit you’ve had, and so on and so forth.

It is defined in terms of “bigger and more”, of “go big or go home”, and often focuses on scaling for the sake of scaling. I know founders who were perfectly happy with their businesses but then suddenly felt discontent because someone else told them they could make more. I’ve seen businesses that’d been growing at a steady pace suddenly speed up unsustainably after an injection of “bro motivation.”

Let me point out that I’m not against building big businesses or keeping at it because you love entrepreneurship. I’m not against working hard and dedicating a lot of your time to a goal. I have often wished – and sometimes still do – that I could be that person who goes tunnel vision on a project until I’ve reached some Big Audacious Goal.

But I’ve realized that I’m not, and that there are many other entrepreneurs for whom success doesn’t equal building something big fast.

A shame, right? This would make for a much more controversial article if I were firmly against something.

Instead, I am for something.

For an alternative way of viewing entrepreneurial success that works for me and how I want to live and feel on a day-to-day basis, not (just) in the future.

A perspective that sees successful entrepreneurship as entrepreneurship that is an integrated part and supporting of a fulfilling life, rather than a precursor for it.

What if it’s not a matter of choosing how much we focus on building our future and how much we enjoy the now, but a matter of building our future in a way that is joyful, purposeful, and gratifying as we go about it?

I’m not talking about turning your passion into your business, neither do I think you should enjoy 100% of the work you do. What I do believe is that if you have moments of nourishment, contentment, connection, and joy sprinkled throughout your days, the 20% (and hopefully not more) of the work you don’t enjoy will carry a lot less weight.

Life and business are not two separate things. We don’t hit pause on life when we run our business. Just as much as our business is one of the many building blocks of our lives, “the rest of life” is there with us when we run our businesses.

That big idea we got when we spent an afternoon “doing nothing” on the beach.
The bad news someone texted us the night before that we haven’t fully processed yet.
The motivation we feel after an inspiring conversation about life with a friend.

It’s all there when we sit down behind our laptops.

We’ve already moved past the “live to work.”
But the “work to live” doesn’t serve me either.
I simply want to live, and have work be a part of that.

A Personal Definition of Entrepreneurial Success

When I shared the draft of this article with a friend, she said she’d love to know how I define success for myself right now. I’ll tell you what I told her: I’m still figuring it out.

But I do know two things:

1. Time and decision freedom are crucial to me. They translate into having the ability to work when I want, how I want, with the people I want, and to do so in a way that makes work a fulfilling part of my life, not just something that needs to sustain it.

2. Whatever definition I come up with, it likely won’t match yours, and that’s the point. To not chase what others are chasing because we assume they know better, or because something makes us feel like we should, but to set our own standards and ruthlessly check them against what we know to be right for us.