The gray space in between
Hey Lyle Letter #007
It’s been too long since I’ve written one of my Hey Lyle advice columns. So here goes.
How do you deal with the conflict between choosing a path that will be more lucrative and a path that is more true to what you actually want to do?
Recently, I'm going through the job search process. I feel like I'm just taking the next logical step up the corporate ladder. Some of the roles seem interesting but, for the most part, I'm applying to these roles because they have the highest salaries. On the other hand, I could get a job doing something I actually like, but my salary would be something like 25-30% versus these other roles.
I also worry that these jobs won't actually allow me to pursue my passions in the ways I like to pursue them. For example, If I get a job as a writer, I'll have to write what other people want me to write, when they want me to write it.
Have you had to deal with a choice between more money and more meaning before?
Conflicted in Colorado
One day, when I was in high school, I remember sitting on the stairs at my parent’s house tying my shoes. My dad was on the phone at his desk in the room at the bottom of the stairs. He was a real estate agent at the time. Actually, he was in real estate basically his entire career.
Around that time, he was regularly attending seminar courses run by a sales guru-type guy named Mike Ferry. The strategy Mike Ferry espoused was all about putting yourself out there in ways other agents weren’t—cold calling people at home on their landlines (when those were a thing people had) and door-knocking. Y’know, bothering people when they don’t want to be bothered. My dad had a knack for it and he genuinely seemed to enjoy the challenge.
So there he was, on one of those cold calls that day, going through his typical spiel. After some quick idle chit-chat, he would pivot to his first question, “So, when are you planning on moving?” The person on the other end would usually politely say they weren’t interested or they had no plans on moving anytime soon. But every once in a while he would catch someone at just the right time. Maybe they were about to retire and were looking to move out of state. Or maybe they were growing their family and needed an extra room for the new baby. That first call would lead to an in-person meeting then to an appointment to look at homes until they found just the right one.
This was not one of those calls.
After trying every tactic in the book (mirroring the other person’s demeanor, asking questions with a confident tone to his voice, etc.), he forced a smile and said, “You have yourself a great day,” right before he slammed the phone down and said, “fucking asshole!”
I couldn’t help but snicker. I thought it was hilarious. I still do.
That moment was a turning point in how I viewed my dad’s relationship with his work. Before then, as a young kid, I had assumed he loved working. I knew he took pride in his work. He was clearly good at it. And he spent countless hours—and money—honing his craft. Yet after that day, I noticed how much stress he was carrying.
Years later, after he retired, I asked him if he had loved his work and his answer surprised me. He was grateful that he had found a career that paid well and rewarded him for working harder than the next guy, but he also saw it as a means to an end—a way to provide for our family and make enough to buy nice things and still have a bunch leftover for his retirement fund. He liked helping his clients find their new homes, yet part of him wished that he could’ve flown helicopters for a living as he had during his time in the Army in Vietnam. I wouldn’t say he had regrets, but that doesn’t mean he never thought about how his career could’ve been much different.
I tell you this long-winded story, Conflicted, to show you that you’re not alone. Even those who seem to have it all figured out are dealing with the choice you’re struggling with right now.
Do you pursue a role that pays you more but might make you feel like you’re crushing your soul a little bit each day? Or do you find something that nourishes your soul but makes it harder to splurge on the nicer things in life?
It’s a dilemma I’m familiar with. It’s also a privileged dilemma. The vast majority of people can’t afford to spend time hemming and hawing about where their next paycheck is coming from. So, first of all, consider yourself one of the lucky ones. The ones who have the means to even be contemplating this decision. I don’t mention this to minimize your worry, Conflicted. For me, having that kind of perspective has been helpful during those times when I’ve been in your shoes. But it doesn’t mean your feelings aren’t real and valid.
That being said, I’m going to challenge you on the framing of your questions. It seems as if you’ve created a false dichotomy—a simple black or white choice between two extremes when there’s a gray space in between them.
It sounds like you’re a writer. Just because you work a high-paying job, it doesn’t mean you can’t pursue your passion for writing. Nights (or early mornings) and weekends exist. Sure, you may need to be more intentional about how you schedule your time. And you might not have as much energy each time you sit down to write.
But you can make time for it. I would argue that you have to make time for it.
Don’t be like me and spend nearly two decades of your life letting your creative muscles atrophy. Instead of carving out an hour of your day for creative work, you’ll focus too much on getting to the next rung on the corporate ladder. Too much on adding another digit to your bank account. As you commute to the office, you’ll daydream about pouring yourself into a writing project. You might even take a vacation and tell yourself that you’re finally going to sit down and start it. But then you’re too exhausted from working your tail off and you don’t have the energy, so you don’t pick up your pen or open your laptop. Then the next thing you know, it’s almost twenty years later and you’ll look in the mirror and realize you’ve frittered your time away and now you have to make up for it.
Your creativity is too important—and it needs to be nourished. Don’t let it perish.
In my mind, the answer to your situation is simple, Conflicted. Work isn’t everything. Life is a complex, messy, and beautiful thing, and there’s more to it than just trading your time for money. So find a gig that makes you enough to live comfortably and still gives you the time and space to do you and experience all that your one, singular life has to offer.
Thanks for reading. If you want to ask me for advice, you can do so anonymously here.
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