A note for anyone who thinks their success today is defined by how things play out tomorrow
I have a friend who is a medical director and feels stressed because he doesn’t own a clinic to sell when he is ready to retire. I have another friend who started a purpose-driven business that thrived for 5 years and then fell on hard times after the pandemic. She’s working tirelessly now to keep the lights on. I know a third person who has climbed to the top pay tier managing a hospital but can’t find the next career opportunity because everything she looks at requires a pay cut. All these people feel trapped because their next step doesn’t appear to be greater than the last one, so they think they must be failing.
As an entrepreneur, I’m frequently asked “What’s your exit strategy? Who will want to buy Uncharted or DrAndyRoark.com when you are not a part of it?” That question used to really bother me. It was clear that people were judging my current performance based on how they imagined “the endgame.” If they thought I was doing something that would result in a grand finale, a financial windfall, or a golden parachute, then they were impressed. If they didn’t see that, I perceived they were suddenly unimpressed with my work or felt that I was naive. “He hasn’t really made anything lasting,” I imagined them thinking.
For a long time, I bought into this line of thinking. Making something that can grow, persist, or create value for someone else in the future takes planning. Thinking ahead and working towards creating that type of opportunity for yourself is a good strategy. If you have the option of doing something you love AND you can grow this venture significantly, build upon it, and/or sell it to retire in luxury, then you should probably do that. If you can make your next step bigger than your last, and you are still excited about that step, why wouldn’t you?
Thinking and working for the future just makes sense, but there is another truth that also needs to be said (and almost never is). I want to say it to you now. Here goes … The idea that your success is dependent on the next thing you do being “bigger” than the last thing you did is complete bullshit.
I mean that. If you are doing work that you find meaningful, supporting yourself, and putting a bit away for the future, then you are not failing. Think of all the people who have put in 30 years working for some company and then retired. Were these people failures because they did a thing and then just … stopped? I don’t think you can make that case. What about the people who entered the hustle game, decided they hated it, and left to pursue something quieter and less lucrative. Did they fail?
If you start a non-profit, make the world a better place, and support yourself for 6 years before closing it down and doing something different, you have nothing to be ashamed of. You have created a meaningful chapter in your life where you learned, grew, and improved the world. The same is true if you start a business, grow it, and then give it to your employees instead of selling it. If you decide to take a pay cut to change career paths, that’s also not an obvious mistake.
After all, judging your life based on whether the hourly rate you could charge for your labor has unerringly increased feels pretty arbitrary. Why not judge your life based on things like:
- How much have you enjoyed the time you‘ve spent on this earth?
- How many times have you reinvented yourself and explored new things?
- How many people have you mentored, impacted, or inspired?
- How often do you get out of bed excited to go to work?
- How many workdays flew past because you felt truly engaged with what you were doing?
Think about it – if you were talking to people at a nursing home, who would you be more impressed with? The person who says, “I steadily made more money my entire career,” or the person who says “I made the most money working as a veterinarian in Boston. I had the most fun teaching veterinary technicians in Philadelphia, and I made the biggest impact working in a shelter in Albany”?
I’ve talked to a lot of people recently who feel trapped. They don’t like their job and they feel like starting over somewhere else means “failure.” I assure you it does not. Failure is you breaking down. Failure is you coming to a place that isn’t working for you or that is making you miserable and staying there. Failure is regretting the thing you didn’t try for the rest of your life.
So, if you have done what you are excited about and now that time is coming to an end, that’s okay. If you made a business that supported you for a while, allowed you to pursue a dream, and taught you a ton of life lessons, it’s okay to shut it down and go do something else. If you want to pursue a different career path and can handle taking a pay cut to make that happen, do it with your head held high. (Relatedly, if you see an opportunity, but it doesn’t meet your needs, passing on it is also not a failure. It’s just what needs to happen.)
This idea that success means never taking a step down or backward for any reason is destructive and stupid. At the end of it all, 99.9% of the people who didn’t ever pivot, backtrack, or flat-out change course ended up stuck doing something they wished they could get out of but felt powerless to escape. We are all exploring a vast wilderness. We are not climbing an endless mountain, tethered to the person in front of us with nowhere to go but directly up. You can have an adventure that simply comes to an end before a new one begins. The important thing is to relish what you have been able to do instead of torturing yourself over what you think should have happened in the future.
