The Freedom Ladder

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.

Does this resonate with you?

  • You have a one-hour commute to the office every day. You use the time to listen to podcasts, but you don’t feel like you’re moving forward.
  • You work from 8am-5pm. You work with good people, but stuff takes forever to ship. Sometimes your contributions never see the light of day.
  • You get home at 6pm. You eat dinner with the family. If you’re like me, you’re already feeling sleepy at this point.
  • After dinner, you do chores, homework with the kids, and put the kids to bed. By this point, you’re positively exhausted.
  • 9pm. You and your partner finally have time to chat. For me, this often looked like us both laying on the couch, being half-asleep.
  • 10pm. If you’re smart, you’re already getting ready for bed so you can wake up at 6am tomorrow.

You're looking for time to work on your own projects but you don’t have any wiggle room.

How to build your ladder to freedom

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.


These are the steps that worked for me. They might not work for you.

Also, I've had plenty of times when I felt hopeless, tired, and stuck.

Your definition of "indepedence" might be different than mine. Some people want to make their own products. For others, freedom means working remotely. Pursue the option you want!

My freedom ladder looked like this:

Gain some leverage at your office job

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.

Get some freedom from your office job

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.

Apply for remote jobs

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.

Get a remote job

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:

  • We could buy a house reasonably close to downtown
  • I was able to rent an office downtown for a reasonable cost
  • It's close to skiing, mountain biking, lakes

Make small projects, and release them for free

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. 

We called it Product People and our whole objective was to create something that was “ours” that was outside of our full-time jobs. (Our first episode was October 15, 2012)

Doing the podcast, and releasing it for free, had a bunch of benefits: 

  1. We were meeting all these amazing founders (Hiten ShahNathan BarryRuben Gamez).
  2. Our show started attracting an audience. We were helping people learn the basics of product design, execution, and marketing. 
  3. We were starting to see opportunities where we could help this audience even more. These turned into blog posts, episode themes, and live workshops.

Create a small project, and charge money for it

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)

Keep showing up

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)

Build something bigger. Charge more.

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.

Quit your job once you have a sustainable audience and revenue

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. 

Here is my revenue report from 2016, 2017, and 2018.

I'm the co-founder of We do podcast hosting and analytics for folks like Basecamp, Taylor Otwell, and VH1. You can hear about our journey on the Build your SaaS podcast. Want to start your own podcast? Read my guide.

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!

Justin Jackson

Originally published on August 12th, 2016. It's been updated since then.

Published on June 7th, 2019
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