A Lesson from an Unlikely Source

Read time: 7 minutes

Welcome to The Ascend Archives, a weekly newsletter where I share a story about a transformation, revelation, or change in thinking that has helped improve an aspect of my life.

This is Part 2 of my fly fishing adventure so check out Part 1 for some more context on the trip!

I’m sitting with 7 other guys at a gourmet restaurant in downtown Portland.

Everyone is catching up on the past year and making jokes about previous trips.

“My gear has been sitting in the closet since our trip last year, how about you?”

“How many fish are you going to catch this year? You’re due for a massive Steelhead.”

Here I am trying not to ruin the vibe but also not be the awkward guy lurching in the corner. I try to relate with the guy who lived in Chicago and another guy who I recognized from listening to him on a podcast.

*clink* *clink* *clink*

Barrett [the trip host] gets our attention, “Welcome to our 3rd annual Steelhead Fly Fishing Trip! We’re going to kick it off by going around the table and each talking for 3-5 minutes. Most of us know each other, but we have two new guys so instead of regular intros I want everyone to talk about who you are outside of work and one question or intention you have for the weekend.”

We go around the circle and I’m the next one up. My heart is pounding and my hands are sweating. Doubt about whether I belong creeps in. I say a little mantra in my head… you’re already here, just be yourself.

“Thank you all for welcoming the random guy from Twitter to the group. I’m glad you all seem like normal dudes so far… This past year has been full of adventure and exploration which was a catalyst for me coming on this trip. I play pickup basketball, train for triathlons, and do a lot of travel... My question for the trip is essentially, “What’s next for me?” I quit my job 7 months ago and proved that I could make enough money to cover my expenses but I feel like I’m at an inflection point. So what does phase 2 of my business look like going into 2025?”

I tried going into the trip with no expectations. Worst case, I will learn how to fly fish, see a new part of the country, and have a good story to tell. Best case, I get some life changing insight or make long lasting relationships. Most likely, I’ll meet some cool guys, have fun, enjoy time in nature, and maybe something good comes of it down the road.

Everyone finished giving their intro and now I had some information about each person to help engage in more conversations. I walked out of dinner feeling settled in with the group and ready for sleep.

We had an early 5 AM departure for the Deschutes River.

—

In the morning we drove 2.5 hours to Madras to drop off our cars and meet with our guides. Over the next 3 days, we would boat down ~30 miles of river, stopping at the best fishing spots along the way to attempt catching iconic Steelhead Trout, and camping overnight by the river.

Waiting for us were 4 drift boats. Two of us per boat with one guide to steer us and one bagger boat with a guide who carried all our stuff down the river. Each day consisted of a morning and afternoon fishing session. We rotated who we fished with each day so we could hang out and talk with different guys in the group.

In session one, I got paired up with Tony. As we started floating down the river, I started thinking to myself:

What’s the vibe going to be? Do we just talk about fish? About life? About business?

I let Tony take the lead. I didn’t want to come across as pushy or annoying. But of course, the conversation started to flow organically. We were just two dudes in the middle of nowhere with a cooler full of beer, floating down a river full of fish ready to get caught.

I knew these guys were super smart and successful entrepreneurs and that this trip served as a way to get deep about our lives. But at the same time, these are just normal guys who want to get away from their businesses, families, and society for a few days to hang with the boys.

The entire first day was very chill. The guides taught me the basics of fly fishing. I learned about how Steelheads are born in the Deschutes River, swim out to the Pacific Ocean for 2 years, and were then returning to the river as we were trying to catch them. Most of the day was spent shooting the shit about fishing, sports, and our lives back home. Then on Day 2, Barrett announced before our morning session that we would have a discussion that night about a question that he wanted us to think about…

“What is one thing you have done or are proud of from the past year that you want to be known for but haven’t told anyone or been recognized for?”

When we got to dinner, I was ready to go and volunteered to answer first.

I shared that while my big question for the trip was to figure out what’s next, I’m proud of how I have lived this past year with massive uncertainty. I became comfortable answering the question “What do you do” with “I’m not really sure, I’m still figuring it out”. When people ask if I see myself staying in Austin for a while, I answer “I don’t know, I’m just taking it 6-12 months at a time”. When people ask if I’m worried about losing a client and not being able to pay the bills, I answer “Yes, but I’m confident that I’ll figure out a way to make it work”.

My next steps are unknown. And I’m proud of that.

We continued going around the circle and people shared how they built strong relationships with people in their community, made positive steps in their relationship with their wife, and became more intentional with their kids.

All things that should be celebrated but go unnoticed.

About an hour after I shared, the circle came around to Dylan (one of the guides and owner of the fishing excursion company).

Dylan had taken a massive risk in the past year. For the previous two trips, he was the lead guide but as an employee of another company. But thanks to support from Barrett, he left the company and started his own company.

Dylan, sitting directly next to me, put his hand on my shoulder and said “I completely resonate with what Andrew talked about in dealing with uncertainty and having to lean into it. This past year has been one of the most uncertain of my life with my business, my relationship, and other moving pieces. I have so many unknowns. But one thing I’m proud of is that I learned there will always be uncertainty. So given that, I try to only focus on two things: doing what I love with people I love. I found that this year with this business and these people I’m doing it with, so the rest of the unknowns either don’t matter or take care of themselves.”

Chills fired down my spine.

Do what you love with the people you love.

That was the answer to my question of what’s next.

This past year has been about finding what I love to do. Being outside, traveling, playing sports, spending time with friends and family, pursuing entrepreneurship, and writing stories. I’m doing all that and will continue doing that. But for business specifically, it solidified in me that I haven’t found the people I love to do it with - business partners and teammates who I can riff on ideas with, work late nights with, and go to war with to accomplish a common goal. I’ve been going at this stuff on my own and it’s been lonely and at times unmotivating.

I found what I love but now I need to find the people I love to do it with.

Final Thoughts

I came to this trip excited to meet these impressive entrepreneurs. The potential to learn from them and build relationships with them could level up my business and life.

But sitting at the airport at 11 PM waiting for my redeye flight back to Austin, the one thing I couldn’t get out of my head was Dylan’s quote. Not something I learned from Barrett or one of the other “successful” guys on the trip, but from our fishing guide.

We can learn from everyone around us: a younger sibling, coffee barista, employee at work, or fishing guide.

Dylan and the other guides were as much part of the trip as us 8 entrepreneurs. From the conversations on the boats, at meals, and hanging around camp - they were in on all the inside jokes, fish discussions, and competition smack talk. They had just as much pride if not more in having the most fish caught in their group.

I’m grateful for Dylan’s insights on life and all the connections I made during those 3 days. Oh and this massive Steelhead Dylan helped me reel in!!

Stay tuned for Part 3 to hear how I’ve applied this lesson to my business since the trip!

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew