Before You Quit

This is part of an ongoing series on leaving a corporate career to join an early stage startup. You can find the first installment here.

A few years ago I left a corporate career to join a startup. If you are thinking of doing the same, here are a few questions to consider first:

Do you have a strong financial foundation?

The financial impact of quitting your corporate job can be significant. Do you have a mortgage or kids? Does your partner work? Can you go unpaid for a year? Financial uncertainty is a reality in early-stage startups. If you are in a relationship, you’ll need your partner’s full support. Read that last sentence again.

Can you deal with the work environment?

Think about how you like to work. I shifted from a lively workspace — my old group had 150 people in an open-plan office — to working mostly from home. Days immediately had less structure and less human interaction. Not everyone can stay focused or enjoy work in this type of environment. Can you make the adjustment?

Are you willing to get involved in anything?

In large companies, roles are typically specialized — you’re a business analyst, an engineer, a marketer — and you get support from teams like HR and Legal. Since small startups don’t have the same breadth of expertise in-house, everyone is required to stretch. Regardless of your role, you could be asked to research employment agreements, create revenue projections, or set up an ad campaign on Facebook. Flexibility and versatilility are a must. Are you comfortable with this?

How strong is your commitment?

Early stage startups are a roller coaster ride and they can fail for many reasons — product issues, people issues, financial issues. If things aren’t going well, how long will you stick it out? For some, it’s about how much time to wait for success. For others, it’s the cumulative gap between new and old pay. Ultimately, it’s personal, but its worth thinking about in advance. At a later stage startup I am familiar with, after missing one payroll by a few days, a bunch of their engineers quit. At an early stage startup, more commitment is necessary.

Before you quit

To develop a better understanding of what you could be getting yourself into, here are a few practical things you can do:

  • Find old colleagues who have made the transition and talk to them
  • For one month, spend a day a week at a local WeWorks. Talk to people
  • Subscribe to Startup Digest’s weekly reading list. It is strongly curated, short, and covers a diverse array of topics
  • Attend meetups. Every week in major cities there are quality interviews, presentations, and panels. They offer the opportunity to learn, connect with people, and develop a feel for your local startup community
  • Watch Silicon Valley
  • Stop reading Techcrunch

If you are thinking of founding your own startup, try to stay working in your corporate role as long as you can. Move things along on the side for as long as makes sense.

Midnight: Another 5 star review? You’re still counting?

A few personal observations

While still sitting inside the corporate world, it’s hard to visualize all the ways your life will change if you make the leap. Here are some things I noticed in the months after I quit:

  • Stepping out of the corporate world — where it could take 6 months just to get a server — into the land of mobile development and cloud deployment required a big mental reset. I felt like I’d spent the last 10 years in a technology cave.
  • I found myself working every weekend, which I was fine with it, but you need to watch out. Don’t neglect friends and family. Stepping away from work is not being irresponsible.
  • Working in a small or distributed team meant there was less energy around me. I found myself retreating to email and Slack. Don’t fall into that trap. Use the phone. Meet people face-to-face. Otherwise you will find yourself in need of socialization.
  • I also had to travel more — to help with fundraising, meet the extended team, and talk to partners. Travel is not that glamorous, and I still feel like my productivity drops by half when I am away.
  • Oh, and forget about vacation. I took a few days here and there, sure, but I always had my laptop. You feel like everything stops when you are gone, and at a small startup that’s never comfortable.

There are of course many upsides to working in a startup. Here are a few things that stand out for me:

  • I get to regularly make decisions that materially impact our company and our customers. It can be a little scary at times, but it’s incredibly rewarding.
  • I work in a startup with a mission that connects with me strongly. Frankly, it’s refreshing. Corporate missions often feel secondary — something tacked on in response to an article like this, and with results like this.
  • I find myself in a constant state of learning. In the first 18 months, I had to come up to speed on behavioural economics, machine learning, regulatory issues — COPPA, PCI compliance, and banking regulation — and the tools and technologies in the mobile development stack. All of this was directly applicable to my day job.

Final words

I share my experience in the hope it helps you make a more informed decision. Remember though, no two startups are the same.

Next up, we’ll look at how to assess a startup that you are thinking of joining. We’ll also introduce you to a third cat, Tony’s sister Roxy.