The Freedom Ladder

You’re here because you’re not satisfied.

You’re good at your job, but you're tired of the way things are. You’re stuck in traffic for two hours a day. You’re working on projects that never ship. You have a new baby in the house, and you’re not quite making ends meet.

You want life to be better. 

Sidebar: being in traffic almost killed me. It wasn’t the danger of getting into an accident (although that possibility was always there). What I mean is that it sucked away my will to live. Sitting 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.

There is hope. There’s a ladder to independence and I want to tell you about it.

Note: many of my contemporaries have a similar framework.

Rob Walling has The Stairstep Approach. Amy Hoy has Stacking the Bricks. And Sacha Greif has The Spiderweb Strategy. They all share common advice: start small, and grow through iteration.

My aprroach has subtle differences; largely related to me having a big family, and starting the process in my 30s. Use what works for you!

Here’s your problem:

  • 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.

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:

  1. I got some freedom from my job. My wife and I had our first child at 22. I had been running my own business since I was a teenager. But with the birth of our daughter, we decided that I would get a full-time job, and focus on that until all our kids were in school. However, there were still opportunities for me to free up 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 7am until 3pm, so that I could beat traffic and save almost an hour a day. Finally, I was able to get a full-time remote job which cut out my commute entirely. (This was 2012)
  2. I made a small project and released it 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. (First episode: October 15, 2012)
  3. I built an audience by helping others. Doing the podcast, and releasing it for free, had a bunch of benefits. First, we were meeting all these amazing founders (Hiten Shah, Nathan Barry, Ruben Gamez). Second, our show started attracting an audience. We were helping people learn the basics of product design, execution, and marketing. Finally, we were starting to see opportunities where we could help this audience even more. These turned into blog posts, episode themes, and live workshops.
  4. I created a small product and charged for it. One worrisome trend I’ve seen lately is that everyone wants to start big. They want to do something huge and put a huge price tag on it. Here’s my advice. Whether you’re consulting or building a product: 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. (First product, Amplification, released in October 2013)
  5. I kept 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)
  6. I built a bigger product and charged 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.
  7. I continued to scale my audience and revenue. Marketing for Developers opened a lot of doors. I spoke at MicroConf in Barcelona on that topic in August 2015. I created a version for non-technical folks called Marketing for Product People. I grew my newsletter past 10,000 subscribers. I answered questions and built a following on Twitter.
  8. Finally, I quit my job. 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 my wife and I decided to take the chance. I started a new podcast, called MegaMaker, that chronicled my journey.

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.

How to get started

My recommendation? Don’t start by trying to find the "perfect business idea." 

Instead, choose a group of people you’d like to serve. (Learn more about choosing an audience here)

If you have questions I’d love to hear from you. Reach out to me on Twitter, or join my newsletter.

Justin Jackson

Published on August 12th, 2016
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