Dear Owen,

By now you’re old enough to know most of my life story. I’m not just “dad,” I’m also the guy that people stop on the street and say, “Hey!  Aren’t you that blogger guy with the beautiful wife who became a billionaire in her late 30s?” And yes, Owen, technically that is a correct way to describe me, but before I became “just” the trophy husband to your lovely mother, I had a career. Many careers in fact. You may not know this, but before that first Rob Complains About Things propelled me to profits in the tens of dollars, I had the following jobs:

• Paperboy
• Golf Range Ball Picker Upper
• Camp Counselor
• Telemarketer
• Intern
• High powered attorney
• SAT tutor

That’s right, my boy, I’ve done it all, and along the way, I’ve learned many lessons—mostly because I fucked so many things up. Because I don’t want you to be one of those spoiled billionaire brats, here’s some advice that may help you as you advance through your career:

1.  Don’t listen to anyone else.

You will hear a lot of different things about the “right” thing to do. In fact, that’s precisely what I’m doing now. Remember that what’s right for one person may not be right for you.  A wise woman once said, “Don’t go chasing waterfalls.”  Well, that’s the best career advice you’ll ever get (if by waterfalls TLC was referring to money, prestige, or someone else’s approval).

Looking back through old pictures, I’m blown away by how clear my career intentions were. At various points in my life, I made it clear that I wanted to be:

A carpenter:

A tiger:

and a naked cowboy:

Yet somewhere along life’s journey, that path got twisted and turned and tied up in knots, and I ended up trying to fulfill some unrealistic vision of the perfect career. I’m not sure where that vision came from, but it was misaligned with what my gut was saying to me (and at times that gut was a massive force).

So, in a quest for a real corporate career, I wound up in some rather odd places. My first job was to call mutual fund companies pretending to be someone else so that I could pass judgment on their customer service department. I was essentially a rogue member of the Jerky Boys (or a humorless corporate behemoth version of the Jerky Boys).

Next, I ventured into the high-powered world of technology as a telemarketing sales rep. I cold called hundreds of people a day, but spent the majority of my time developing my writing skills by drafting uproarious emails to my friends.

Fed up with the nausea that developed when I told people I was a telemarketer, I left this illustrious career to attend law school. I’d show them, I thought.  Lawyers are prestigious! Who could hate a lawyer?  I’ll go work for a big law firm and lead a life filled with happiness and riches. Instead, I developed mild cases of anxiety, depression, isolation, OCD, and the Sunday mopes. That’s when I followed in my old man’s footsteps and became the SAT King of the East.

I hope you get the point here. Listen to your heart and follow your real passions. If you want to become

a fireman:

A 1920s paper boy:

A British Guardsman:

Or a Run DMC:

Well, I’m not going to stop you. Go with it!

2.  Do the things that you want to do.

You come from a long line of entrepreneurs and risk takers. Your grandmother had a business that was built on a foundation of eggshells (literally). Your aunt is a Millennial Workplace Expert.  (I know, sounds made up, but it really was a thing back in the Early 2010s). If you want to be the world’s next great egg painter, then you should. Don’t worry about what other people will think of your career choices. If you like it, it will work.

A brief anecdote about your grandfather: According to legend, Grandpa Buddy finished college and decided to follow in his old man’s footsteps.  Although it seems impossible and contrary to every established fact you’ve learned about the old coot, Big Papa Buddy was at one time going to be a dentist. That means that he must have taken at least one science class in school.

Well, Big Papa Buddy got so far in his pursuit of a dental degree that he applied, enrolled, and matriculated in Dental College. Papa Buddy was moving along “the path” until the day the professor introduced them to the drill. When he started to drill—and take this with a grain of salt because the veracity of Papa Buddy’s stories is always in question—Papa Buddy accidentally drilled right through the tooth he was working on and then through the table in the lab.

Later that day, Papa Buddy informed your Great Grandpa that the quest for a dental degree was coming to an end. He became a dental school dropout, spent a brief period of time working in a hippy dippy poster shop in New York City, and then went on to have a legendary teaching career.

The point of this story, Owen, is twofold:  1) Don’t do anything just because I say to or because you think it will make me happy, and 2) Don’t become a dentist or come anywhere near my teeth with a drill.

3)  Embrace the hard parts.

Any time I’ve started a new job, tried to master a new skill, or pursued anything with vigor, there came a time when it got difficult.  Like way more difficult than I had initially thought possible. When that moment comes, it will seem simpler to take the easy way out. The “easy way out” can take many forms, but the most common are quitting or stagnating.  If you settle into your comfort zone because it makes your job easier, then I promise you will hit a point where you hate it. It’s worth fighting through loads of challenges to break through to a level of competency that you could not achieve by staying in your comfort zone. Another wise woman once said:

I stole that from an episode of Girls (who probably stole it from somewhere else). See, Owen, I’m not afraid to borrow liberally from TV shows with gratuitous nudity and sexually suggestive language.

Anyway, when you hit the point where something gets hard, that’s the point when it’s really important to push yourself to the next level. If you don’t make the effort at that moment, one of the following things will happen: You’ll quit; You’ll stagnate; You’ll get bored; Others will pass you by. All of those are bad options.

Fight the urge to be complacent when you’re “good enough,” and try to be better. It’s the hardest thing to do because it means stepping out of the comfort zone, but it’s worth it because when you get to that next level, you’ll feel like that effort was worth it. You will also be really good at whatever you were working on. I mean, just look at how far my stick figure drawings have come since the beginning of this blog. Do you think that’s a coincidence?

4.  End on a high note

Sometimes you have to know when to walk away.  Even though I literally just said you have to push through the hard parts, sometimes it’s not worth it.  If you hate something you’re doing, or feel like you’re doing it just to appease the desires of others, or for the money, or for the chicks, then it’s probably a bad idea. Walk away. There’s no such thing as career momentum if you’re momentuming towards something you don’t want.

I’m going to take some of my own advice right now, and end this before it gets even longer and shittier than it already is. So peace out, Owen. I hope you find a career that allows you to support me and my poker habit when I’m cooped up in that old person’s home eating mashed up peas.

Peace out!

Love,
Dad

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Editorial Assistant: Brandie Smith/ Editor: Catherine Monkman

Photos: Courtesy of Author