On Taking a Leap of Faith

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On Taking a Leap of Faith

For the past three years, I’ve felt like the only way to get off the cliff of my life was to dive off the edge. By all standards, life was good—stable, well-paying job; loving family; time to spend at leisure. To most people, it probably didn’t seem like I was standing on a cliff at all.

But deep inside, I felt deep conflict.

I graduated college with honors and was blessed by God to step into what would be a dream job for most people. The salary was good, the company was prestigious and close to home, and the work was interesting.

However, the role was in software engineering, something I had decided not to study because I didn’t want to take that career path. After taking four years of computer science classes in high school, I realized I wasn’t as keen on programming computers as I first thought. (I’ve always been more of a “superuser” or problem-solver than a developer.) As such, I got my bachelor’s degree in information systems, sort of a parallel track but with a much greater business emphasis.

But when presented with what seemed like a golden opportunity straight out of college, taking advantage of it seemed like the “best” option. It seemed like “destiny”.

But deep inside, it didn’t feel right.

Long story short, I tried my best to make the job my own, but could never work it out. Even though I performed well, I still felt out of place, like I should have been somewhere else. I compared it to a square peg trying to fit into a round hole. It just didn’t work.

The obvious solution would be to find a better-fitting job, right? And yet, that presented its own set of problems.

Even though I didn’t like my job, I couldn’t make myself quit. Quitting goes against my very nature as a person—especially when it comes to school or work. Not only did I feel I’d let people down and leave them hanging, but I felt I’d be jumping off the cliff into the abyss.

I am also not an impulsive person by nature. Very rarely if ever do I “impulse buy” something; I always do my research first. If anything, I am prone to “analysis paralysis” by evaluating every possible option in any given circumstance. (Will the gas savings of the F-150 EcoBoost outweigh any repair costs I wouldn’t have with the FlexFuel V-8? Would an SUV suit me better? Do I need a gas-guzzler at all?)

And, I couldn’t think of (or find) any other job that could fill the gap. I either seemed unqualified or overqualified for everything that did seem interesting. The jobs that I probably was qualified for would have been like what I was trying to get out of—not solutions at all.

So, take my anti-quitter nature, my anti-impulsive nature, and my inability to find a “better” job, and what do you get?

You get a guy caught in limbo.

And because of that limbo, I started thinking. “What kind of job or career could I get myself into and find some peace and fulfillment in?”

That thinking led me into exploring entrepreneurship. I had worked as a contractor for a local entrepreneur during college, and loved almost everything about it. I had flexibility, a variety of tasks to perform, and a degree of authority.

But what I enjoyed the most was the feeling that I was making a difference for him, his business, and his clients’ businesses. And over time, that feeling changed to fact: I knew that I was making a difference.

A little over a year after I started my job, I took him to lunch and picked his brain. I learned how he started his business and absorbed all the advice he gave me. (This was all stuff I should have been more attentive to when I actually worked for him. At the time, I was just a nerdy college student who thought he’d rather clock in and out for a paycheck.)

I did my own research. I took stock of my skills, and what skills I could learn. I calculated and budgeted. Most importantly, I prayed. Hard.

I started a scrappy “side gig” rebuilding and rebranding my former boss’s websites. Both were in serious need of attention because they didn’t represent his businesses very well. One had been hacked or otherwise compromised and featured lots of hidden ads for Eastern European drugs. (All legal ones, I’m sure.)

At his recommendation, I formed my LLC. I set up business profiles. I started connecting with people and got invited to a networking group (virtual due to COVID). I acquired a few clients from the group. I started connecting with more people and acquired a few more clients. I received referrals. I did as much work and self-promotion as I could, given constraints on time and energy.

Somewhere along the way I realized I was finally getting some lift beneath the wings of my business. I also realized that to get off the ground, I would have to go all-in, full-time. That was the only way I could manage existing clients, new clients, and my own self. It was also the only way I believed I could be taken seriously as a business owner. I had to “go pro”.

I got real cerebral and philosophical during this period (yes, more than usual). I read a lot of self-improvement books and learned about philosophy and meaning. I spent months poring over Ecclesiastes. I was searching for something—direction from God, some deep insight, something—that would give me direction. Should I stay or should I go?

Like many of life’s big decisions, the answer was not clear-cut. That’s also assuming there was an answer in the first place, but I won’t go down that rabbit hole. But, I came across a few ideas that gave me guidance and comfort.

The first one came from Dr. Jordan Peterson. To paraphrase something I heard him say in an interview, “The devil you do know isn’t necessarily better than the one you don’t.” To put it another way, it’s easy to shoulder the burden you carry here and now because it’s familiar and predictable. Though it’s heavy and unwieldy, you don’t have to worry too much about it because it’s not likely to surprise you. That’s complacency—accepting the status quo.

But there might be some other burden out there that is lighter and easier. And yet, if we just keep trudging along with the burden already on our shoulders, we’ll never know. (In writing this, I’m reminded of Christ’s words in Matthew 11:30: “For my yoke is easy, and my burden is light.” Note that he does not ever say that we’ll be unburdened—I think bearing a load is necessary for a sense of meaning—but he does say that working with him is easier.)

The second one came from the author Steven Pressfield. In his book The War of Art, Pressfield says that the thing you fear the most is probably the thing you need to do the most. He calls that mental, emotional, spiritual, and sometimes even physical force that stops you Resistance. Resistance rears its ugly head whenever you want to do something brave, adventurous, or worthy. Resistance can take the form of fear (of failure, of the unknown, of rejection) or of procrastination. Our minds are wired to make us avoid situations that could cause us pain or ejection from our position in society. Being in need or cast out from our clan make us vulnerable. And vulnerability means we could perish.

But we have to learn the difference between legitimate fear or common sense that stops us from making poor choices (you could kill yourself popping a wheelie on a busy street) and taking calculated steps out of our comfort zones that could improve our lives (starting a business, asking a girl out, learning to dance). If we completely disregarded those warnings, we’d be dead. But if we heeded all of them, we’ll be resentful and unfulfilled.

These things and more mixed around in my mind, day and night, as I contemplated my next moves. Everything pointed towards the path I was preparing to go down, but I still felt unsure. I knew the devil where I was. Resistance tried to convince me that I really was just fine where I was.

And then I heard the third idea.

I was meeting with a client one Friday afternoon. As we were talking about how I could better help her organization, she asked me when I was going to leave my day job. I told her I had a date in mind, but still wasn’t sure.

She looked me in the eyes and said something I’ll never forget: “When you take a leap of faith, God will either catch you when you fall, or teach you how to fly.”

This, coming from a woman who literally lives her life taking leap after leap, told me what I needed to know.

So, despite familiarity, Resistance, and my rather weak faith, I jumped. I’m now suspended somewhere out over the edge of the cliff, arcing forward and slightly down as gravity acts on my body.

But I feel great, because I know I’m not leaping alone. God is with me. Even if I shouldn’t have made the leap, I know He’ll catch me. My trust is in Him.

And even though I believe He’ll teach me how to fly, I believe it’s my responsibility to build the wings. So if you’ll excuse me, I’ve got work to do.

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