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, its 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:
- Are Braintrust and Tout the right products? Will it make money for me?
- Do I need to focus on one product to succeed? Is now the right time to focus?
- To make these products a success, do I need to bring on a co-founder? Is now the time to build a team?
- should I look for funding?
- should I apply to ycombinator? 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.
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. Its 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 3 weeks at a time. In about 6 months time, I’ll re-evaluate which idea should get less and which should get more attention.
- Spin up independent consulting for 50% of my week. If you know someone that needs help with UX, UI, Product Design or just to take an idea to a prototype, I’m your man, please send them my way (tawheed at gmail).
- 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.