I joined the software industry in 2008. I was 28.
Previously, I'd been a branch manager for a non-profit. My office was ten minutes from my house, and I set my own schedule.
But now I had a new career in software. It meant a bigger salary, but it also required me to commute downtown every day. That was a 45-minute drive.
That drive almost killed me psychologically. Waiting for red lights to turn green, trailing thousands of other cars into the city. Sitting, motionless, in the car. I used to envy the folks whizzing by me on their bicycles. By the time I got to the office, I was completely drained.
A few weeks into the new job I heard about 37signals. I started reading their blog, listening to their podcast, and I read Getting Real. Everything they said resonated with me. I remember being especially impacted by this post by Matt Linderman:
I don’t commute. I work from home. And I love it. I think of it as getting an extra hour a day. Add that up over the years and it’s a huge chunk of my life that’s given back to me. Not to mention the emotional toll that’s saved from not doing a rush hour commute, especially one on public transportation.
My commute was making me miserable. So decided to do something about it.
Initially, I asked my boss if I could work from home. The answer was "no, we have a culture that requires the whole team to be at the office."
So, I started looking for other options.
I read 37signals' blog religiously. Every time they had a job posting, I'd take notice. Eventually, an opening in customer support became available. I decided to apply.
As a fan of their work, I knew what they were looking for. I took a day off work and wrote my cover letter.
I sent my email, my cover letter attached. Then I waited nervously.
The next evening, I got this email from Jason Fried:
I flew to Chicago and spent the day with their team. It was like a dream come true.
Jason and David offered me a job. I said yes.
But, when I told my current employer I was leaving, they said they'd promote me to Product Manager and give me a raise if I stayed. I knew that additional money would be a gamechanger for my family. We'd recently had a new baby, and had moved into a bigger home.
So, I turned Jason Fried down. That was one of the hardest decisions of my life.
I enjoyed my new role as Product Manager and having more income was helping my family, but I was still miserable. I wanted more freedom: the flexibility to live, and work, where I wanted, and the ability to set my own hours.
Over the next few years, I was able to gain more leverage, and eventually, get the freedom I desired.
If you're in a similar situation, there's hope.
You're looking for time to work on your own projects but you don’t have any wiggle room.
Have you ever seen a painter use a scaffold? It’s a ladder you construct to get from ground level up to the elevation you want to be.
Getting freedom from your job is similar. You figure out how to build a scaffold, and get yourself closer and closer to your goal.
My freedom ladder looked like this:
From the time I showed up at that first software job, I was ready to prove myself.
I would observe my boss. Whenever it looked like there was a task he didn't want to do anymore (or couldn't, because he was too busy) I would volunteer.
Want someone to go with you to sales meetings to demo the software? I'll do it!
This helped me earn a reputation as someone who was helpful. It also helped me become indispensable. Soon, I was doing a variety of tasks that would be difficult to do without me.
This gave me leverage for future discussions with my boss.
I found opportunities for me to free up more time, specifically that one hour commute. First I tried taking the bus and working on projects on my laptop.
Next, I asked if I could work from home one day a week (this saved me two hours!).
I also tried working from 7 am until 3 pm, so that I could beat traffic and save almost an hour a day.
The best time to apply for a job is when you have a job.
Applying for other jobs is almost always a good idea. It keeps you sharp, and it shows you what other opportunities are out there.
For many people, having a remote job will give them the freedom and flexibility they desire.
In 2012, I was finally able to convince my boss to let me work remote.
I was able to move to the Okanagan in BC. We picked this location because:
Once I was working remotely full-time, I had an extra 10 hours per week (because I wasn’t driving anymore). For the first time in a long time, I could pursue side-projects. It was right around this time that Kyle Fox approached me about doing a podcast together.
Doing the podcast, and releasing it for free, had a bunch of benefits:
Lots of folks want to start big. They want to do something huge and put a huge price tag on it.
Here’s my advice: start small, and charge a small price for it.
I realize this goes against the advice of “double your rate” and “charge more.” Once you have more experience you should increase your rates. However, if this is your first product (or your first time doing freelance work) you have to start small. You haven’t built trust yet. Building a reputation takes time. One of my favorite ways to get started is to do a small workshop. Convince five people to show up for a live event, and charge them $10 each.
(My first product was a little e-book called Amplification, released in October 2013)
Once I realized I had some traction in the product people space, I focused on it. I was insatiably curious. I would research, ask questions, and do experiments. I wrote exclusively about making (and marketing) digital products. I started a weekly newsletter. (2013 and 2014 are when people started inviting me to speak at events and guest on podcasts)
Once you’ve done a series of smaller engagements (products or consulting), and you’ve built a reputation, it’s time to go a bit bigger. In 2014, based on the profile I’d built in the product community, I was able to quit my full-time job and start consulting full-time. I consulted for teams based in Colorado, Portland and San Francisco.
In 2015, I built and launched my biggest project to date: Marketing for Developers.
Marketing for Developers opened a lot of doors. I was invited to speak at MicroConf in Barcelona. I grew my newsletter past 10,000 subscribers.
My original plan was to continue consulting work until the summer of 2016. Then, the startup I was working for got acquired.
I had a choice: I could go out and get more consulting clients, or, I could try to stop consulting and focus on “making my own stuff.” Ideally, I would have had more consulting income in my bank account before I made the leap. However, all my kids were in school full-time, and I decided to take the chance.
Currently, in 2019, I'm building a podcasting platform with my friend Jon Buda. It's called Transistor.fm. We provide podcast hosting and analytics for creatives, brands, and organizations.
We've been working on it since the beginning of 2018. We hit $15k in MRR in May of 2019.
It's important to note that this is a long journey.
It took me years to go through each of the steps listed above.
Years of investment culminated in a product that was generating enough revenue to make the leap.
I hope this helps!
Originally published on August 12th, 2016. It's been updated since then.