I recently took a sabbatical from contract mobile application development. I had been doing it for 2.5 years straight, and although I can't argue with the pay and schedule (fully remote, over $100K/yr), I did eventually feel like I wasn't learning much on the job and that I needed to do something kinda risky to go somewhere new in my career.

Also, on a more practical note, when you're spending 40 hours a week prodding object oriented frameworks (or worse, React Native) and hoping they'll do what you want them to, that doesn't leave a lot of time for trying new things, learning, and growing. So it's pretty easy to get pigeonholed as "the mobile guy" and then basically stagnate until retirement.

Now that I have planted that somewhat dark thought in your mind, I would like to humbly ask if anyone here has tried taking a sabbatical from paid work.

If so, how long did it last? What was your goal? Did you start and finish a project during your time off, or did you simply take time away to "study up" on something different and new?

Did it work? When you came back to the workforce, did you do so in a capacity where you could work on projects you're passionate about, using techniques you actually support (instead of saying you do to get past a job interview)?

My plan is to try and work half the year for someone else, half the year for myself. I think if I can time some of these contracts to start in July and end the following July, I'll have two years with income below the Roth IRA yearly income threshold (~$110K/yr). Then if I can consistently save and invest half of my income, I'll gradually slide into a position of never having to contract again, or perhaps have a project of mine gain enough momentum to replace the income of full-time contracting.

But I am actually hoping others have tried a better strategy than mine. After all, it seems kinda extreme that I have to periodically end contracts early, or that I literally have to retire just to put enough work into projects I actually care about. Maybe that's just how the work world is, but I suspect there's something I'm missing. I do know some people who have fulfilling careers, and they haven't had to do anything as drastic as what I'm doing.

Hi Ted,

TL;DR Cultivate multiple streams of revenue by spending years combining two skills 'only you' can pull off.

Where I Am

Your question is perfect timing because I am on sabbatical. My work history is here. This is a long story so grab some coffee! I'm also just talking about myself so it's going to come off a little bleargh and pompous.

*Ahem* I've been out of the workforce since March -- I made my decision back in January. I've used this time to build on Handmade Seattle, and to try and ship some software.

Handmade Seattle

I'm grateful Handmade Seattle (HMS) has been successful so far. Obviously not enough to replace my whole income, but definitely a reasonable slice through leftover profits from ticket sales and public and private donations. I like to reinvest those profits back into the business, with the hopes I can hire staff and give myself a salary one day.

HMS is the result of combining two skills in an unusual way:

1. Sales.

2. Systems programming.

I'm half-joking about sales :P I have a deep love for human interactions and am overtly social. People people people. I can enter partnerships, buy the right insurance, work hard on selling tickets, and talk to people all day. Last year I was always on the phone with the Seattle Center or onsite.

Note that my contributions to Handmade have been "on the side" since 2014 when I became a Twitch moderator for Casey. Six years later, a single tweet by Carmack has changed my life. Seriously. The level of support we're getting makes me confident we can rent a large conference hall after the pandemic, and from there on Handmade conferences may become a mainstream staple.

Shipping Software

In the past I've tried and failed to ship software, but now in my late 20's I've sobered up and understood this is slow and takes obscene amounts of grit.

During this sabbatical I'm making my own terminal, and I hope to give "Early Access" in early 2021. It's still a prototype, but the skills I'm combining are:

1. Career experience with gamedev

2. In-depth-ish knowledge of terminals. I obsessed over the literature for a year or two.

I'll discuss what's hopefully interesting about my terminal later, but I can at least say it's hardware accelerated, based on Vulkan. That's not a thing elsewhere, AFAICT, and I really enjoy working with the Vulkan drivers vs the OpenGL ones. I've endured frustrating tutorials and made my own library to succeed so far.

Selling a tool is a viable path to a revenue stream. Look at 4coder, RemedyBG, Code Clap, etc. While I won't be able to sell something valuable for a while longer, there is hope :)

What's Next?

I will likely look for a job within the next 1-3 months. With the conference -- and one day (soon?), the terminal -- I have more leverage to find a fulfilling career and negotiate a contract that lets me run side-businesses. I will also hunt jobs that allow 4-day work weeks. Then if I ever go solo again, it might be for good.

I hope my story helped. I still make huge mistakes. Still get afraid. Still don't know if I'll succeed financially the way I want to. That said, I'm closer now than I've ever been. So that's something.

In your case, you clearly know how to make a good living. You take risks. You have strong mobile experience (check.) What's a second unexpected skill you can bring to the table?

Best of luck,
Abner

I love hearing these stories. Thanks for sharing yours!

I can definitely chime in and say you're on to something with this notion of combining two skills only you can pull off.

I spent my 20s more or less being a snowboarding bum. I lived in various ski resort towns working odd jobs, really just trying to work as little as possible so I could spend the afternoons getting really good at hitting snowboard jumps.

It took about five years of consistent practice to get to a level where I was regularly hitting the biggest jumps in the terrain park. At the peak of my abilities, I was doing double backflips, 720s, gnarly stuff like that.

I spent summers in New Zealand because I was that crazy and that addicted. I think there was a year or two where I didn't experience summer at all because I would just fly to wherever it's winter.

Obviously, unless you're like a mega pro who was born with a snowboard strapped to your feet, there's not any money in snowboarding. And even at that level, there's always someone better, someone younger, someone who came up through the right channels.

I was pretty happy with what I had accomplished, but I knew I needed to move past the snowboard bum phase of my life.

And one day, I saw these kids playing with these plastic dice on the gondola. They had tricks on them. So you would roll a trick and try it, challenge your friends, that kind of thing.

This was right around the time smartphones were becoming mainstream, so it occurred to me that you could put this on phones as an app.

Long story short, that's how I launched my first product, Snow Dice. My team then took the idea and expanded it to skateboarding and skiing. It is the result of doing exactly as you say, combining two skills only you can pull off.

Nobody I knew in the snowboarding world had the same knowledge of the sport plus ability to ship software. And there were plenty of people who could ship apps, but none of them were in the sport or could understand it as well as we did.

The idea was always for the product to be more than just a software version of the dice. You can use it to learn what the tricks are. It has difficulty settings, so you can try things near your ability level. There's even an advanced feature that puts tricks together in a line, something nobody was doing at the time.

Anyway, this was some time ago, but the crazy thing is the product still makes consistent revenue. The idea is kind of timeless. I've been collecting that dividend for almost ten years now. It hasn't really grown much, but it doesn't show any signs of slowing down.

People say there's no money to be made in mobile, and that's half true. If you aren't drilled down and focused on a specific kind of customer, you'll be competing with everyone.

For me and my team, it worked because we were the customer. We knew exactly what our friends would want in that product, and we built it for them.

I'll have to chew on what you've said though. Over the years, my interests have kind of changed, but I've also wondered about some new ways to use software to train people up in the sport I love.

For anyone reading this, the coolest thing about doing any of this isn't the little bit of money you get every month. Oddly enough, my apps have somehow gotten onto over 100,000 smartphones, and it's not too uncommon to run into my customers on the chairlift.

Small things add up over time.

Edit: I really appreciate the stories, so I felt the urge to add to the thread. So thanks for the awesome stories to you two!

I probably spent just as much time on sabbaticals as on the job. I have pretty much always been contracting / solo-consulting so it came somewhat naturally but it was also intentional. Did it work? Yes and no.

I was very lucky and the second real consulting gig I landed was with that amazing crazy project which basically taught me everything, it was like a lottery ticket in terms of learning (I didn’t do uni fwiw). When I was in my early twenties I was super confident and knew I would be a good programmer but I actually didn’t have any experience obviously, I just knew that I was good at trying hard basically. ;-) In that project I learned how to program for real-real, write device drivers, assembly programming, CPU uarch optimization, architecture, ...., even some business skills, and most importantly it was a project that did everything in ways that were radically different from the mainstream (huge C monolith projects run by equally huge companies and armies of devs) but could compete even though the team was tiny compared to the competition. So... lots of foundation and confidence-backed-by-experience instead of confidence-backed-by-youth gained.

Then I did my first sabbatical. When I told my relatives they thought I won the lottery and I must be some sort of big shot now (nope). I just wanted to do a bit of soul-hacking but after a couple of months I felt super bad for not “earning” and I started to prototype this high-performance (think 10G-100G) IPsec gateway. After a year in “sabbatical” I applied for a grant to try to turn this into a product, and I worked another couple years on this. I didn’t strike gold here. Short version: I am not a sales person, nor did I really do market research before hand.
On the plus side: I did make a pretty good product and learned a ton about cryptographic protocols and other related domains.

One important thing to note, I feel, is that basically what I did—and this will be a repeating theme—is to work for free (invest in learning and R&D) to then do something professional with it. So... is that economic? Invest a year of your own time and then give the gained experience possibly to a company that possibly might pay you slightly more? Not saying its a bad idea, but basically I have to consider my salary divided by two because I invest half of it straight back into sabbaticals where I basically... work for free.

Which brings me to “time some of these contracts to start in July and end the following July, I'll have two years with income below the Roth IRA yearly income threshold”. Yeah, those are thoughts from my head. ;-) I think for me this this is a fun life style, however my accountants seem to be always worried about me when roll this way. :D

So back to the story... I did my second sabbatical where I learned Rust and embedded programming, some soldering, because the hardware-software interface is something I wanted to get into more, and rust seemed like a worthwhile thing to know. To learn Rust I ported the amazing project I mentioned earlier to... well Rust. This’ll be important later on.

Financially I could be doing better by this time, so I took a job at a startup that turned out to be a disaster because I didn’t vibe with the bossmang. On the plus side: I learned a LOT! I learned about control theory and signal theory. They were doing embedded controllers for super-accurate lasers and control and signal theory is how you drive those beasts.

Being a bit chafed I went on my third sabbatical where I learned Verilog/HDL, designed and implemented a CPU core and ISA from scratch, and wrote my second assembler and my first SSA-based compiler to compile a statically typed subset of Lua targeting that ISA/core. Because... I’d really like to maybe work with a company on building a real CPU some day? And compilers... well I was just putting that off for too long.

At this point I realize that this... drive to build things to know how they work? It’s all due to my imposter syndrome from not doing uni. Whenever I see a person writing about amazing stuff they did at uni, like design a CPU core in HDL? I get the urge to one-up them. Silly. But hey, learning things is fun right?

So now the theme I introduced repeats: I could be doing better financially, and I start working with a startup, and what do they want? A thing based on the Rust port of Snabb I wrote in my second sabbatical. Bam! Business genius move right? Or did I just work for free and amortize this now on a job? If I were better at marketing myself, maybe I could have done the thing on-payroll in the first place?

So... to sum things up... I think sabbaticals are great fun and my way to learn stuff. I don’t know if what I’m doing is the best economic strategy tho. I could definitely do better from what I can tell from the greater IT-sphere. OTOH I can’t say it worked out badly either. Might be that I’m only landing gigs that I like because I happened to put in the work during sabbaticals, and mostly I think its yet to be seen. I’ll let you know when I land my dream gig and it was all due to the careful planning, preparation, and self-directed hacking and impossible otherwise. ;-)