June has been a tough month for me. My last day at my day job is fast approaching and although Tout and Braintrust are both generating some revenues, it’s not close to where I want to be to feel financially secured.

I’ve come to realize that quitting is easy. Accepting another a job offer is also easy.

But, taking the leap to a sound footing is hard and requires you to make a lot of tough decisions. Transitioning from a day job to being on your own is a seriously scary thing.

In contrast, making the decision to quit my day job back in March was a no-brainer. I reflected on what I wanted to do with my life, and I knew in my heart that building startups is what I love doing.

Knowing what you want is important, and sometimes hard, but now that I’m working through getting what I want…well this is where the rubber meets the road. And…it’s hard.

To craft my plan, here’s how I went about doing it.

Answering the obvious questions

I started with answering logistical and concrete questions like:

  1. Are Braintrust and Tout the right products? Will they make money for me?
  2. Do I need to focus on one product to succeed? Is now the right time to focus? Note: I think both of these ideas are pretty strong in my opinion and it is unlikely I will kill either. I see no reason I cannot continue to grow both in the long run with short periods of focus on each.
  3. To make these products a success, do I need to bring on a co-founder? Is now the time to build a team?
  4. Should I look for funding?
  5. Should I apply to ycombinator?

Although thinking through these questions was helpful, and talking to people gave me a ton of insight, I realized that I was getting very fixated on the financial questions, and even worse was jumping to common solutions like “oh.. Just go look for funding.”

Transcending to the higher-level questions

I paused.. And pulled myself up to the larger questions at play… What is it that will make me happy? How do I want to be spending my day? What is really the larger goal at play here?

Fortunately, I already had the answers to this. When I set out on a conscious journey to build a startup, I wrote down my personal goal: “Be able to do whatever the fuck I want.”

It was funny. After reading that, it all became so much clearer. I’ve been having to prepare for months if not years to become non-dependent on an employer.

Do I really want to turn around and get funding? Do I want to take the leap from one master and jump to another?

All the little questions became irrelevant.

Of course I don’t want funding. Of course I should work on my ideas freely. I don’t want to take on any masters. I want to be Bootstrapped, Profitable & Proud (inspired from the series that 37Signals has been running).

Hopefully getting what I want

And so, armed with the clarity of knowing what I want (be able to do whatever the fuck I want), I defined my transition strategy.

I know where I want to be…just read any one of those articles on the 37Signals blog.

And I know I can’t get there in one fell swoop. It’s going to take some steps, and some transitions. But on a 10-year timeline, I think I can get to a great spot (hopefully). Here’s what my transition looks like:

  • Focusing on each of my ideas three weeks at a time. In about six months time, I’ll reevaluate which idea should get less and which should get more attention.
  • Spin up independent consulting for 50% of my week.
  • Scale back on expenses. This means getting rid of my beloved BMW, moving to a smaller (but still cozy) place, and spending less money on going out.

I’m excited. I want to be Bootstrapped, Profitable, & Proud. I want the freedom to do whatever I want. I want to be my own master.