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 it make money for me?
2. Do I need to focus on one product to succeed? Is now the right time to focus?
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?

   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.

After much introspection, I found that while I banged out certain tasks very easily, I consistently kept on putting off certain tough tasks day after day. As I drilled in a little deeper, I really came to face the fact that I was simply scared of taking on some of those tasks.

Doing a project with a team of one is tough. In actual startups with teams, you can usually turn to your partner to talk through certain things that you get stuck on. This does not happen when you are trying to think through problems and pain points in your head, regardless of how good of a problem solver or thinker you are.

Faced with this problem, I came up with an aide to help me think through these tough tasks. The whole idea is to drill down into a task that I’ve been putting off in a systematic manner. Whenever I find something that I’m scared of tackling, I pull up my MacJournal and start writing a journal entry with this template:

What’re you trying to accomplish?


This is where you put a simple one-line sentence describing your intent.

What do you need to accomplish this?


Usually, I write out a list of what needs to be done. Think of these as sub-tasks. Don’t think so much about how these will be done, just focus on what actually needs to be done.

What’s easy to do?


Simple enough right? Take the stuff you need to do, and list out the things that are easy to do. Try not to regurgitate the items on your sub-tasks list, but make it more of a free flowing thought process.

What are the roadblocks?


Start reading through what you’ve written. At this point, it really should be becoming clear in your head why you’ve been putting this task in the first place. But don’t stop now. This is the section where you just start listing out all of your roadblocks, all of the things you’re scared about, all of the things you don’t know (how to do). Again, don’t worry so much about how you’re going to solve these problems; instead, focus on the what the actual roadblocks are and list them out.

What are some possible solutions to each roadblock?


Alright, if you’ve been diligent so far, you should be feeling a lot better about this task now. Hopefully you are already feeling excited about truly understanding this task and at this point your mind is flowing with ways to solve the roadblocks you’ve identified. List them out, don’t worry as much about whether they can actually be executed on, but focus more on possible solutions. You don’t want to go completely out of touch here, so I’d recommnd you list possible solutions in the order of feasibility.

Action Items


This is where it should all come together. You should read over everything you’ve written, digest it, and finally come up with some real action items for yourself to tackle this task for real.

This technique has been working amazingly well for me. I’d love to hear from you if you decide to try it out.