The Future

Being just a little bit on sabbatical all the time.

A few weeks ago I got this reminder in my calendar:

Sabbatical Return Reminder

I knew the date was coming up, but even so it felt like a bit of a surprise. Six months flew by! Hard to believe it’s been half a year since I left my job.

Six months ago, on my very first blog, I got a comment from someone (Zach Burt of Code for Cash) who clearly knew more than I did about starting businesses. He said:

People tend to overestimate what they can accomplish in a year and underestimate what they can do in ten years. So your six month timeline has me nervous for you, but I can tell you this: you can definitely build something that generates revenue in such a timeframe. —Zack Burt, Code for Cash

Thankfully he was right. Barely.

I made my first dollar from place card me just a few weeks before the six month clock ran out. Amazing how a single dollar has had such an impact on my perception of success versus failure.

The product builder funnel

I made it! Just barely. (graphic from my first blog post)

Anyway, Zack’s comment now has me wondering… what could I accomplish in ten years? And, more importantly, shouldn’t I try to give myself the space to answer that question?

This has led to some amount of soul-searching and future-planning that has me continuing to try and figure out what the heck I want to do with my life. And I think I have, at least, a short term plan.

Here are the constraints / priorities I’ve landed on to help guide my future:

  1. I really like the reduced responsibility, flexibility, and work life balance of sabbatical life (especially compared to CTO life)
  2. I want to continue to learn new things and explore self-driven projects
  3. I need to earn enough revenue to live on
  4. I miss doing what I would consider “meaningful” work—that is - trying to do something good/important for the world.
  5. I’d like to continue to be involved with Dimagi, a company where I invested the first 10 years of my career and saw grow from 3 to 130 people

Fortunately—and I really can’t understate how fortunate I feel to have all of the flexibility afforded to me—I’m optimistic that I’ll be able to achieve all of this.

So here’s my current plan:

  1. I’m going to go back to Dimagi in a new role at 40% capacity starting later in October. Jon, our CEO, has chosen the title “Chief Accelerator” which I love—partly because it’s a cool title and I love the idea of accelerating things, and also partly because it’s got a bit of that cheesy “synergistic” type of vibe that is funny if know you Jon. Anyway, hopefully I’ll be able to use my knowledge, skills and experience to add a ton of value to the organization while avoiding some of the bureaucracy and stress that got me into trouble in the CTO role.
  2. I’m going to spend about 30% of my time doing freelance consulting for other organizations. This will help pay the bills and get me exposed to other teams and projects. I’ve been doing it for a few months and have had overall positive experiences.
  3. I’m going to spend the remaining 30% on my own projects, including place card me, writing, and hopefully a bunch more side projects. Mostly because it’s been super fun, but also because I think I still have lots to make for the world and lots to learn in the process.

Seem too good to be true?

It might be.

I’m operating under a lot of assumptions—that I’ll be able to keep Dimagi time to 40% without getting sucked in, that I’ll continue to be able to get attractive freelance engagements, and that 1-2 days a week will be enough time to make meaningful progress on my side projects. Any of these could be totally wrong, in which case my plan kind of falls apart.

But if it does fall apart I plan to adjust things accordingly and design a new balance that works better. For me, the key element here is that, for the first time in more than ten years, I’m not just running on whatever track was laid out before me, I’m the designer of the career that I want.

And now that I’ve gotten into this mindset it seems crazy that I ever didn’t think of it this way.

So here’s to a wide open future. One where I’m just a little bit on sabbatical… all the time.

Sabbatical Return Reminder

High five for permanent sabbaticals!


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