Suffering and Achievement
Why (some of us) feel like we can't have and deserve good things without suffering
I jotted these notes down from a coaching session with a founder:
SUFFERING = ACHIEVEMENT Can’t have good things and deserve things without suffering.
The founder had built a successful and profitable company, yet was struggling to decide when he had done enough to deserve to take a break.
Can you relate? I find this deeply relatable. For some reason, I feel guilty whenever I spend time doing something I genuinely enjoy.
Suffering is a successful strategy
It’s not uncommon among high achievers because largely the strategy is been a successful one.
From a young age, success rides on our ability to turn away from the things which engage us (e.g., the Stanford marshmallow experiment), and turn our eyes to the work at hand. Stopping play and doing homework. Not partying and instead studying late into the night. Spending the extra hours to polish the narrative before the presentation. Forcing yourself to grit through the less pleasurable things yields great results.
It’s also true that suffering is a pretty essential part of growth. If you follow the research on grit and growth mindset, gaining mastery over a topic requires deliberate practice, which by definition is not fun. It’s not enough to be talented, you have to put your equivalent of 10,000 hours of work into improving.
In short: achievement in early life means gaining mastery over our impulses. You get wired to conflate successful with the suffering of practicing self-control.
When is a startup a success?
Where this strategy begins to fall apart is when you ask: When have I achieved enough? When do I get to stop deferring and start experiencing good things?
What gets confusing about building companies is that success indicators are so sparse, and there isn’t a ceiling to achievement. You get stuck wanting to achieve via the respect and estimation of others.
The thinking goes: grind really hard, get a great outcome, achieve success, and then enjoy the rewards.
The suffering/achievement loop especially hits once you get your company to a state where it’s working. If it’s profitable and growing, how can you make it grow faster? If you got an exit, how can you get a bigger exit? The tricky problem here is that along the way, the goalposts move higher. It’s not clear if it’s a success.
When you see herds of startup unicorns in the news, your achievements to date start to feel pretty modest. So you go back to achieving, grinding away, ad infinitum.
If you follow this formula, it’s a path without an end. There’s always the next ascent, ever higher.
Finding another path
I struggle with the pressure to follow the path still. After leaving my last exec role, I felt an immense amount of pressure to continue upward to the next fancy title and company. Instead, I chose the less orthodox path of starting Notejoy and later opening an executive coaching practice. By choosing to do this, I get to do the most interesting and meaningful work of my life while avoiding the hours and politics of company building.
But emotionally, the wiring runs deep. I struggle with the feeling that I’ve wandered off the path. Part of me buys into the formula that achievement cannot come without suffering. When I have the kind of workday where it just feels easy, sometimes I feel guilt for not working on something “more serious” or with “more impact”. Or, other days where I see my peers in the headlines, I feel FOMO for opting out.
I haven’t solved it, but I do try to answer the guilt by asking, Where does the path lead after all this achievement? For me: I get to do meaningful and interesting work and live a life aligned with my values. I’m pretty sure I’m exactly where I should be, but I know I’m not alone in not being able to shake this feeling.
I asked the founder from the coaching session: What happens when you achieve success?
To him, it meant being free. Free to live a life filled with pursuing his interests, and enjoying it.
But he didn’t deserve it yet.
This is essay #7 in my series to conquer my fear of writing.
I think at some point in your life you realize that you have already achieved all your childhood dreams, and then enough is really enough. Now I try to pass on these lessons to my kids and the next generation.