What I wish I knew before I quit my job

Before I quit my job at Confluent, I was worried about taking the plunge.

Everyone likes to use this metaphor because it focuses on what’s so scary in the beginning: passing through the weird transition between employee and employer.

But after the last 16 months of building my company, this metaphor doesn’t sit right with me.

It’s not like you take a scary jump once and then you’re good.

It’s more like plunging in over and over and over again. Cycles of fear, courage, and calm.

When you signed up for this newsletter, I promised I’d give you real startup advice from my own present-day experience. So in this post, I want to share with you what each of these cycles has looked like for me in the 16 months since starting ShadowTraffic.

I’ll give you a real quote out of my journal, and then share what I’ve come to believe is the right long-term way of thinking about whatever cliff I was standing on.

Day 1

Ugh, what am I even doing? I just quit a great paying job and now my product idea sounds incredibly stupid.

In the beginning, many bad ideas sound good, and many good ideas sound bad. No one has a crystal ball.

Run a good product validation process, ideally in less than 6 weeks, and you won’t have to worry whether you’re on the right track. You’ll know the answer.

After the first customer

I got a customer, but it was so hard! I honestly don’t know if I can do that again.

The first customer is always the hardest. You closed with them no established credibility, and if we’re honest, an incomplete product. So if you got one, there’s an even stronger probability you can get the next.

Watching early adoption

I got a few more customers, but they’re not yet using it for a critical, sticky use case. What if my product always feels like a toy? How bad would that feel?

Almost no one immediately adopts new tech for mission critical use cases. Trust is incrementally earned, week by week. This is true for every product, and every company needs to fight for reputation.

Silence

Have I plateaued? What worked to acquire new customers isn’t working anymore. This is scary.

Every company hits a plateau. Multiple times!

Instead of fighting it, embrace it a skill you need to get good at. You can’t predict when you will plateau, only that one will come in the future. And when it does, you’ll be more talented at working your way through it.

Approaching renewals

How long will my customers stick around? What if they churn?

If you’re regularly meeting with your customers and doing everything you possible can to support them, you made the right expected-value move with your time. Sure, you’ll lose a few from time ot time, but you’ll win in the long-run by being great at customer support.

Periodically

All of my friends are making way more money than me doing much less work. It feels bad.

Do you have something else you would have rather been doing?