Guys' Trip: How to Refocus on What Matters Most

By Kyle Depiesse

Transformation often happens in the most unusual of places. I've experienced it in my own life and I've witnessed it in the lives of so many incredible humans I've surrounded myself with. It's in these moments when we get the beautiful gift of perspective to zoom out and b

• Language: English
• Publisher: Kyle Depiesse
• Release date: Dec 21, 2021
• ISBN: 9780578338750

Book preview

CHAPTER 1

BACKSTORY

NOVEMBER 28TH, 2013 … 3:30 AM

It’s pitch black out and a little chilly outside. Would you expect anything different in Minnesota for this time of year?

Nope.

As I get out of bed, I try not to awaken my wife. I tiptoe over to the closet and scramble to find work clothes to wear while using the flashlight on my iPhone (why didn’t I lay my clothes out last night, I think to myself). After making a questionable fashion decision on my outfit for the day, I walked into the kitchen to fill up my coffee cup thermos and grab anything I could find to snack on during the drive.

I like my coffee strong. But even the most caffeinated cup of coffee would not be enough to wake me up from my eleven-year professional slumber.

My family was visiting my wife and me from out of town. It was, after all, Thanksgiving Day. But while family was visiting, I was driving into work. In the industry that I was in at the time, retail, Q4 is a huge deal. Black Friday, the day after Thanksgiving, was even a bigger deal. But was it such a big deal that I needed to leave my family at 3:30 am on a holiday? At the time, I was convinced that yes, indeed it was.

You need to be the first one in the office and the last one to leave.

You need to volunteer for any extra projects, so you are viewed as a team player, the one who gets promoted.

If you want to climb the corporate ladder, you should do the types of corporate ladder climbing things. Even if that means you must put your personal life to the side. It’s just for a little bit, a season. Or is it?

So, I get into work, and I’m the only one there. Who else would be up at this hour and on this day? Well, surely this will look good, I thought to myself as I considered how others would perceive me, especially those in the more prominent offices than mine (which wouldn’t be too much of a challenge considering I had a cozy spot in the cube farm).

I got my five hours of work in that day and proceeded to drive back home, grab lunch and then take a mid-afternoon nap for two hours to catch up on sleep. It was a pretty selfish gesture, but this wasn’t the first time I’d done it. Often, we expend so much time and energy that we unintentionally give what little is left over to those we love the most.

It wasn’t the coffee that woke me up; it was upon reflection that I realized I had been sacrificing my personal balance sheet for my professional one. I had reached my limit; this was my rock bottom, and I was burned out, lost, and confused.

Looking back on this pivotal day in my life, I can see all the warning signs leading up to that day. I crawled my way out of the hole I dug, it took a long time, but I did it. And I have led groups of other high-performing men on bucket list experiences that helped them REFOCUS on what’s most important in life.

How did I get here?

That’s a question worth going on a journey to answer.

RANDOM LAKE, WISCONSIN (HOW RANDOM)

Born in a small town in southeast Wisconsin, I was the middle of three boys. My father was a carpenter (50 years!), and my mom worked part-time while raising us boys. As a result, we were encouraged to be as active and involved as we could with extracurricular activities. And I’m thankful for that, and my school years were some of my best years. I look back on them with fond memories, and it’s something I’ll encourage my son to do as well—sports, choir, band, musicals, plays, clubs, etc.

After high school, I attended UW Green Bay and got an undergraduate degree in Business with an emphasis in Finance. I like numbers (nerds unite)!

A few days after graduation, I had back surgery to fix a herniated disc and pinched sciatic nerve. Yes, at age 22, I had back surgery. So while many of my friends were enjoying the summer, I was laid up and doing therapy for most of the summer.

My first job out of college was with a travel wholesale company. This was WAY BACK when planes were chartered, packaged together with a hotel room and ground transportation, and you’d find out about the deals in the newspaper. That makes me feel old!

As a 22-year-old, I was leading Fam (familiarization) Trips to Mexico. Not a bad gig for a young guy right out of college, except I was leading a group of mostly middle-aged women on these trips. That makes for a lot of exciting stories, none of which I’m going to share with you here! I spent three wonderful years with this company and decided it was time to spread my wings. So I moved from Milwaukee to Minneapolis to work for a large retailer. This was my first experience with a fast-paced corporate culture—quite a shock for a small kid from small-town Wisconsin.

The unspoken culture here was that every 18-24 months, one should be getting promoted. And if you’re not, well, then there might be something wrong with you. I quickly found out that I didn’t fit this model. Round peg, square hole. Anybody else? But at the time, it really bothered me. Why should I have to play this game to get