I was recently asked an interesting question:

“Now that you’re responsible for a broader scope of work and a team, how do
you get over the fact that you always feel like you’re doing a bad job?”

And after thinking about it, I answered truthfully:

“To be honest, I don’t really feel like I’m doing a bad job at all. I used to
feel that way a lot, especially earlier in my career when I was more affected
by imposter syndrome, but now most of the time I actually think I’m doing a
pretty good job given the inputs I have at the time.”

This isn’t because I’ve become a narcissist (I’m pretty sure that’s true). And
it’s not that I always have a perfect vision or understanding of what I’m doing
(definitely not true). It’s more that I’m more comfortable now with the gray
area of not knowing how to do something before I do it. I find myself leaning
into my imposter syndrome rather than let it intimidate me into inaction. By
“leaning in” I mean accepting the reality of how I feel – uncertain – and
forcing myself to take actions to confront and pare down that uncertainty.

A good microcosm for this is public speaking. Do I still feel nervous before I
go up to speak in front of a group of people?
Yes, literally every single time. But the crippling fear of looking stupid or
bumbling my words from years ago has given way to a confidence derived from a lot of
reps and a lot of preparation. Because of Cheekswab
I’ve spoken in front of literally thousands of people over the last 10+ years.
I’ve learned what it takes to make myself comfortable on stage: a good script
and a lot of practice. I will rewrite and practice a talk for weeks before a
speaking opportunity. Confidence in that rigor means that speaking opportunities
now fill me with excitement rather than fear.

Confidence is borne of rigor. And as that confidence at work has grown, the type
of work I’m most personally interested in has changed. I now much prefer poorly
defined or emerging problem spaces over scoped problems because I enjoy the
challenge of putting structure around an unknown ask. I don’t have all the answers,
but I’m confident in my ability to figure them out, especially if I hold myself
accountable to a few key strategies:

1. Practicing sound project management practice.
2. Not ignoring smells.
3. Soliciting diverse feedback via an intentionally cultivated backchannel.
4. Seeking data to verify (or often invalidate) my instincts.
5. Biasing towards action and preferring to iterate on a scoped attempt at
   something rather than ship a perfect version from the start.

I’m not saying I always think I’m right, nor am I advocating for a persona of irrational
egotism. In fact, leaning into your imposter syndrome only works with a healthy
dose of humility, because blind confidence removes the need for any rigor at all.
What I’m saying is that I’m confident in my willingness to constantly revisit my
assumptions, which in turn gives me confidence in good outcomes.

I understand the roots of the original question – management/leadership is much less
deterministic than writing and shipping code, the feedback cycles are either
long or non-existent, people situations resolve much less cleanly than technical
situations, etc. But I still reject the idea that feeling bad about uncertainty
is unavoidable.

Once you acknowledge that leadership is inherently non-deterministic you can
move away from the self-defeating notion that you’re always doing a bad job.
Instead I think it’s more useful and healthy to move towards an actionable,
productive mindset centered around questioning your assumptions, understanding
that good work is iterative and learning from your previous reps.

When you’re working on something you’ve never done before you’ll inevitably make
wrong choices. That’s okay, and that’s the cost of getting out of your comfort zone. The
differentiator in outcomes for those who venture boldly is how quickly they can
identify they’ve made a wrong choice and how much courage they have to course correct.