My Leap of Faith

Photo by Teddy Kelley

Oct 1, 2015: Day 1 of Month 1, The 15-Month Plan.

I had been talking with a few close friends and family members about going out on my own—either forming a small business or just getting a bit of freelance/contract work.

I was frustrated at that time in my life. I absolutely loved the industry in which I spent my days, but my company was holding me back. They didn’t see the value in a more rigid software development process. They didn’t understand that being led to write good code is more morale-boosting than having a trampoline at work.

Understanding the pursuit of such changes in that work environment would only exist as hope and brief periods of masked change, I reasoned the next step was to do it myself. To create my own rigid process. And if I did that while working for myself, I could use such a process to write good, satisfying, and rewarding code.

I also had other interests stepping out from behind my minds’ closed doors. I wanted to push my musical skills to the next level, to form a better sound for my little musical duo. I wanted to start a podcast. I wanted to write more frequently. And I wanted, for Pete’s sake, to finish the novel I’d been working on (and off and on and off) for the better part of five years.

At that time, I was bringing home a salary that was dramatically less than what I was worth. (I know we all think that for ourselves. Today you can verify it! I did, and I wasn’t even close to the 10th percentile on the generic Software Engineer II salary distribution in Cincinnati.)

In my conversations about going out on my own, I was hesitant, nervous, unconfident. I’d often hear remarks to my words like, “Well, make sure you have six months salary saved before you quit.” Other responses sounded more dramatic and risky, with adages like, “If you jump, the net will appear.” And then there’s my wife, who loves to float in the middle, and she said, “Make a plan, follow the plan.”

I followed my wife’s advice. And thus was born The 15-Month Plan.

Being underpaid didn’t mean I was starving. We were still putting money away. My wife and I figured we could cut back a bit and save enough money that within 15 months I’d have enough in savings to take the leap without needing a client for the first several months. That seemed reasonable.

I was excited. The exit plan was on paper and I had a new life goal.

And while I’d take a few interviews for full-time jobs along the way, I knew the 15-month plan was really what I wanted to do.

Work days got a little easier with the ability to daydream about a future whenever I was frustrated. Either that, or I’d go back to my most recently played album on Spotify—Rain Sounds.

In one of these frustrated moments during Month 3 (Dec 2015), I took to scrolling through Facebook. An ad pulled my attention away (a rare occurrence). The ad focused on matching freelance workers with employers. I knew apps like this existed, though I hadn’t pursued any of them. But that morning of frustration led me to try this one out. Within a few minutes I had signed up and filled out my profile.

A few days later, I received a message through the system, from the owner of the company behind the app. He liked my expertise and he wanted me to help him add features to the app!

What an incredible feeling! He didn’t just want to hook me up with employers. He wanted me to help him build the product. And, even better, he was going to pay me an hourly rate that I set, the rate I felt I was worth!

Soon I began working 10 hours each week for this startup. I was building up some savings faster than I expected. But, even more important, I was having a great time doing the work. It was a really great way of working. There were no emergencies, just loose deadlines built around new feature stories. And it was proving the theory that being completely remote can still lead to good work.

After about a month of working this way, I had a thought. If I could keep this startup contract and move my full-time employment to an hourly contract, I could potentially make this “leap of faith” thing happen sooner.

I crunched the numbers and if the startup seemed stable enough to keep the contract going for several months, and if my current employer would allow me to move to a contract and pay me a rate I desired, I could leap immediately. I could “quit” and would still be making more money than I needed, therefore building up savings right out of the gate.

It seemed risky, but when I laid out those facts to my trusted advisors, The conversations began to lean more toward, “Leap and the net will appear.” To bring even more power behind her words, my mother sent me this video:

My wife was on board, too! I was inspired and (finally) convinced I could do it.

The next step was to dig in and have some real conversations with these people paying me money.

First I went to the freelance startup. If they didn’t have funding this whole thing wouldn’t work as I envisioned. I felt them out a bit to gain insight into their runway, and asked about a possibility of bumping my weekly hours. They didn’t share numbers, but I had the impression they’d keep me around as long as they could and, at the moment, business was going well. It’s a startup, it was risky. But I had to be willing to take some risk.

Next, to my employer. The first conversation with my company was super easy. I wanted to go contract, part-time. They had seen it coming and appreciated my honesty. Then they sent the hourly offer. It was half of my minimum acceptable value (and the minimum acceptable value was still 20% less than the startup was paying me). All-in-all, it was about a third of what the startup was paying me (which was still relatively cheap). I was so insulted I almost said no and walked out the door on principle, blowing the whole thing up. But I stayed, we talked it out and they met my minimum value.

But whatever, I had what I wanted and in the last week of January 2016, both contracts were signed, and I stepped up to the cliff.

And I jumped.

I wrapped The 15-Month Plan in less than four months with a leap of faith.

It’s now been another 15 months since I took that trust fall and, as I like to say, I’ve never been happier or more anxious and stressed out. But it’s where I want to be, at least until it’s time to take the next leap.

And while I still don’t know how this will play out, I’m so happy I leapt when I did. That’s why if you tell me you have a inkling to pursue a passion of yours, I will always tell you what I’ve been told.

Leap and the net will appear.


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