This didn’t age well

For years, I was too blinded by hustle culture to take a vacation. Now, I know better.

On the eve of an impromptu family trip to the Bahamas, I got caught up reading some of my earliest blog posts. When I wrote this particular piece in 2018, I was in trouble and didn’t even know it. Like my daughter, my wealth management firm was around two years old and gaining momentum. I was nervous–not nervous in the excited way but in the way where you feel everything might implode at any moment.

Hustle culture gave my anxiety a home. In my blinding grind, I wholeheartedly believed that entrepreneurs did not take vacations; especially entrepreneurs in finance, who raged around town in their fleece vests manifesting their next win. No. Days. Off. But reflecting upon this now, I cringe. Who was the guy who wrote this, and why was it me? 

Let’s start with the title, Vacations are for the Weak.

I must have thought this sounded aggressive and clever, but now it just gives major Chad vibes, as if those words plumed out of my mouth in a cloud of powdered Whey protein. I was so focused on growth, but what about taking breaks makes someone weak? This may surprise you, but I wasn’t conditioned this way through through social media. As a kid, my family vacations were almost always commingled with my father’s work conferences. Any type of paid-for leisure that was not affixed to a work obligation seemed impractical. I just thought that was how everyone did it. But in turn, I never learned how to turn off, because I never saw “off” as an option. Hence…

“I feel like I have no business taking time off right now.”

In all fairness, at the time I wrote this, the bets I placed on my generation’s success were starting to pay off. As millennials, we were finally hitting our stride, making steady progress in our careers and with our financial goals. Each win for a client felt like another notch in my belt, too, but we were still at the stage where they came by surprise. I sat vigil by my email. Anything could happen. Vacations were roadblocks against waiting with baited breath.

“I have a slew of important meetings the second I get back.”

I am not exactly sure what meetings could’ve been that important; it seems ridiculous to think something scheduled several weeks out could be crucial to the point I couldn’t take time off. Heather told me she sympathizes with this one. Early in her legal career, any time a motion deadline appeared on the calendar later in the month, it mentally impacted her every day until she drafted it. This all comes from a place of insecurity. I didn’t have the confidence to believe I could ever adequately prepare for whatever was coming up, and instead, found comfort in perseverating over a meeting from the moment the calendar invite went out until the meeting was over. There’s irony in skipping vacation for poor time management.

“I like to travel, but I am not the type to go long distances with their little one.”

This one cracks me up. Admittedly, we were pretty wound up first-time parents. The way we hovered over our first daughter as a baby and toddler seemed appropriate in the moment, but I now wonder whether it did any of us any favors. One bad trip to Florida was a perfect excuse to keep on working and never travel with her again. And we didn’t for a long time. 

“I’d have a conniption knowing a client request wasn’t promptly addressed within 24 hours.”

Responsiveness is one of the easiest edges a business can have. This is true. But I took it to such an extreme that I’d allow even the most benign requests to interrupt dinner just so I could get it off my plate (pun intended). Setting unreasonable expectations around client communication isn’t good for anyone in the long-term. When people always expect you to always be available, that is the bar you’ve set, and anything less will be a disappointment. Of course, some high-touch clients and sensitive issues are always worth this level of attention. But I lacked the experience to know how to prioritize, so I’d overcompensate by treating everything the same. 

Thank you for joining me on this embarrassing walk down memory lane. Now, I know that vacations are not roadblocks to success. If anything, they help preserve it. Passing on opportunities to rest and recharge is corrosive to your physical and mental health. After running a three-year, pandemic-driven marathon, I learned this the hard way. Because even though my business grew, I am still dealing with the toxic effects of hustle culture that I fused into my daily practices. Shifting my understanding of what busy really means is giving me greater confidence in ways I approach my career and my time. 

More importantly, no matter how hard I work, there will always be meetings, deadlines, and obligations waiting for me. What won’t always be waiting for me is the chance to create memorable experiences with my family. I never want to be the guy that placed his career ahead of fatherhood. There are only so many times I will get to walk my daughters to school or participate in things that matter to them. What I have to lose is far greater than what I have to gain. 

So I guess you can expect a lot more vacation content from me this year. Don’t worry, I’ll be sure to leave my fleece vest at home. You could say that my midtown uniform has changed.

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