Big decisions are overrated (part 2)

Note – You can definitely hop in here, but I recommend starting with Part 1 to understand a few of the references.

In a few months, I will be launching a Facebook page called “Real Life Newsfeed.” This page will share life as it really is rather than just the highlight reel of constant good news, amazing trips, and thriving relationships.

One of the posts I have in mind is a photo of a restaurant closing it’s doors. I’ll share the statistic of how many restaurants close each year, how many go down in Year 1, and include the cautiously optimistic hashtags: #FollowYourDream #ButLikeHaveABackupPlan.

“Follow Your Dream” has become an incredibly popular mantra in the modern internet world, specifically on LinkedIn. There is daily advice out there to quit your job, follow your dream, start a company. Your 9 to 5 is holding you back, you only live once, what are you waiting for!

I can’t say that I roll my eyes at all of these posts because two months ago it had me fully hypnotized. I was sitting there with three business ideas, a ton of writing projects in the works, and was nodding my head watching a Gary Vaynerchuk video. It’s time. I’m going all in. 

In March, I worked harder than ever on all of these projects. Before work, after work. Saturdays. Sundays. It consumed me. I made Captain Ahab and Michael Jordan look like the ideal models for work life balance. I wanted to prove to myself that I could do it; justify that if I quit my job, I could keep up at my current pace, plus add eight more hours a day Monday – Friday.

But, how did this fit into our marriage. My wife is incredibly supportive, but she does it in a rational way. She’s less of the cheerleading, “Chris, Chris, he’s our man, if he can’t do it, no one can!” and more tactical; more alright, well if this is the decision, then this is what comes next. When I said I was thinking about quitting my job, going all in on these ideas, she said, “Ok, but that means we will sell the house, likely move in with my parents.”

In that moment I was like, “I mean, I want the dream, but let’s not get too carried away here.” 

One night, in the thick of this pursuit, she had me write out a list. Ten words to describe who I am. I wrote things like: idea guy, writer, entrepreneur, dreamer. I read them off. Ashley replied, “So, nothing like son, grandson, uncle, friend?”

Oof. Thankfully I had put husband on the list!

My first reaction was that this was a trick question. I didn’t know I was supposed to list off who I am in terms of relationships. But then it clicked that it wasn’t a trick at all. My list was pretty damn accurate. I truly wasn’t thinking about anything other than my projects.

The big decision of staying or leaving my job had boiled down to which will make me “more creatively fulfilled.” Which has more writing. Which is more in line with “following the dream.”

But the thing is, there are way more factors in play in that type of decision. There’s my marriage, family, relationships, house payments, potential for starting a family next year without being too deep in debt, or even continuing to live in the city.

And those are just the big factors. There are also the microfactors too; the little luxuries like being able to spend $30 ordering pizzas vs. slumming it up with the cheapest possible frozen pizza and a ramen noodle side dish.

And that’s where the internet delivers it’s counter punch. If you can’t handle the suffering, you clearly don’t want your dream bad enough. Insert long list of videos featuring billionaires who talk fondly about those lean years and having negative balances in their bank accounts. Was it worth it? Yep. I have ten billion reasons now why I’m glad I never gave up. When the going gets tough, the tough get going.

Hey, good for them. But notice none of those videos were recorded during the actual sucky part. And no videos exist talking about the people who didn’t find the billion dollar pot of gold at the end of the crappy rainbow. We don’t see all of the restaurants and start-ups shutting their doors.

So I started to do my own guerrilla research. I reached out to people via LinkedIn, reached out to colleagues who I knew worked on writing projects on the side, or side businesses. I basically just cold called people and asked for advice. It was amazing how many strangers, people who were really high up at their companies, would take a meeting. I think the trick was I wasn’t trying to sell anything. I honestly just wanted to learn from them. There’s a sales lesson in here somewhere.

What I found were tons of examples of people working a day job, that may or may not tie in to writing but, in each case, they were happy with that job AND happy with their side projects. And happy with their family life. And happy not to be struggling financially. They loved the balance of it all.

One of the people I talked to said things changed for him when he realized the job, or the art, weren’t his sole identity. He was also a husband and a dad. Or how when he thought about what “making it” looked like, he realized there’d still be things to complain about. Editor notes. Negative reviews. Shows being cancelled. There’s always room for “worst self” and “meh self” to weasel their way back in to the equation.

And that’s when the light bulb went off for me. I thought back to the Hope vs. Kansas decision and remembered that what turned things around at the end of my freshman year were the relationships, not any sort of personal success or “following my dreams” fulfillment. It was more important to have great people to share things with than having great things to share.

For example, last week I was at Mariano’s. They have an escalator where you can put your shopping cart and it carries the cart up to the second floor. I was coming down the escalator and looked to my left, saw a shopping cart going up with only one thing of guacamole. Nothing else in the cart. I looked at it and started laughing. When I came home I shared the story with Ashley. “Who gets one thing of guacamole, decides ‘Yeah, I can’t carry this AND ride an escalator. That’s way too much pressure.'”

This seems crazy to say, but I was happier in that moment sharing a story about a container of guacamole riding an escalator than I was at my “creative” peaks in March when the projects were all that mattered and I was running on low sleep, never resting. The same thing a few days ago when I saw a guy in a BMW convertible, texting, blaring the song “Jump Around” at 8:15 in the morning. Again, I started laughing. I wanted to share the story with my co-workers, and eventually share it here on the blog.

Writing in it’s purist form is really just an extension of community. You’re sharing stories with friends; some of whom you’ll never actually meet.

Other examples of a big job decision

Stepping away from my own decision for a second, I wanted to quickly jump over to one of the most common big decisions made about work. This one is about people leaving a job, or taking less hours, to spend more time with their kids.

A lot of people who make this big decision to scale back will end up saying, “This was the best decision I ever made” and, “I wish I would have done it sooner.”

But there’s no guarantee that doing it sooner would have brought the same result. At 30, the job may have provided security, enjoyment, community, purpose, money to put in savings. At 40, those priorities may have changed and the more time with kids factor was enough to win out over the other variables. But part of why it won out was probably related to the financial piece. Thirty-year-old self had 40-year-old self’s back by saving up a nest egg.

And, the thing is, 30-year-old self may not have been thinking about the leaving job decision at all. It may have just been saving up for a boat or a second home. Or took a video gig at a buddy’s wedding and someone else said, “Hey, could you film ours?” then that slowly snowballed into a profitable enough side hustle. Or maybe 20-year-old self met a girl on Tinder who became a doctor and now he’s living that stay-at-home dad life. Past self can accidentally stumble into good decisions for future self.

Just like mindset can change how we view the same exact decision, all of the different variables in play can make some decisions perfect at one age and not at another. These variables also means one person can choose to go part-time, another person can choose to keep working, and both people may end up being legitimately happy with their decision. It’s not one size fits all.

That’s why ten years from now I’ll read this post and say, “What was I thinking? Big decisions are overrated? No, blogging is overrated, I’m so much happier now as an ice road trucker.” (hey, it could happen!)

Big Decisions. Simple Answers.

There’s nothing new about these Medium Rare lessons, I had just forgotten about ’em. And, sadly, I’ll probably forget many more times in my life.

But, in the end, happiness isn’t that complicated. It isn’t an accomplishment, a dollar amount, or a final milestone. It’s a thing of guacamole riding an escalator by itself. Or a Saturday morning, after a week of work, when you’re sitting in the writer’s room, in a condo that you and your wife can barely afford, with a dog who you love (at least 92 percent of the time) nestled under your am, writing the final paragraph to a book that may or may not sell many copies.

In that moment, the best self, worst self, and meh self are all in agreement – hey, these decisions worked out pretty well.

Medium Rare will have posts every Monday and Wednesday through the end of June. Here are the three most recent:

Big Decisions are Overrated (Part 1)

What’s you name again?

The Lost Art of Complaining

Or, if you’re really fired up and want to read more than a 1,000 word blog, hey that’s awesome! Here are a few longer works available for sale on Amazon:

Toilet Bowl – A novel about worry, love, and urinal cakes.

Medium Rare – Where this Medium Rare journey began, published in 2012. 

Moving Sucks – Just in time for moving season!

And if you’d like to subscribe to this blog via email, just enter your email address in the box below or email me directly at Thank you for stopping by, see you Monday!

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