How I overcame imposter syndrome and learned to love not knowing enough

Investors are meant to know more than most, otherwise, how can they make good investments right?

When I was first thinking about changing from founder to venture investor, I was nearly paralyzed by the sheer number of things I didn't know about VC. It seemed that there was no way to make the change without crashing and burning in an embarrassing flameout.

What actually happened is that nobody actually cared in the way I worried they would, and lots of people were willing to help me along the way.

Imposter syndrome is in fact your superpower - use it wisely

Fear of being outed as an imposter is a strong motivator - it was for me. With sufficient time and access to knowledge, you can learn about almost any field in enough detail to get by.

The challenge I faced was getting comfortable with how much knowledge was enough. If you worry too much about being found out, the answer becomes - I need to know everything. This is a huge mistake. You have to discover a happy balance between familiarity and vulnerability.

I found these three approaches helped me get comfortable being an imposter and also using each new connection to expand my knowledge and adjust my perspective.

#1. Develop a sense of comfort in not knowing the answer.

This was the hardest for me. As a founder and leader, it is hard not to be the font of all knowledge. In transitioning to an investor, I really struggled with openly admitting that:

I have never done this before
I don't know the answer to that question - it is all new to me

What I found though, was that people always responded positively to the admissions and were very prepared to fill in gaps for me.

#2. Identify the things you need to know and work up from first principles.

It wasn't possible to be naive about everything.

If you're setting up a VC fund, there are a lot of specific things you need to know and have answers for. This sort of challenge is really well suited to the second approach - learn the stuff you need to learn.

Fund administration seemed to be a dark art, but in the end, it is accounting and law for the most part. If you're prepared to read, learn and work hard, it's the sort of subject matter that you can approach from first principles.

This sort of first principles knowledge acquisition can be very effective, and also has the advantage of discovering different approaches and new techniques - because you got there on your own - not via some tired or outdated pathway.

#3. Develop a system for thinking about and understanding knowledge that can be transient.

Some knowledge can be transient in purpose. As an investor, I often need to spend time getting up to speed in a new area to support a decision. The bulk of that knowledge may not stay with me, but having tools and techniques for collecting source material and developing insights and hypotheses are vital to that process.

Being vulnerable about what I don't know does not come easy - but knowing what I need to know and being open to different ways of learning the rest is extremely satisfying.