Running Toward Fear

Read time: 6 minutes

Hey everyone! I’m adjusting the cadence for the newsletter for the next month because I’m participating in Write of Passage. It’s a 5-week writing cohort where I learn how to improve my writing and get detailed feedback from professionals on my writing. Instead of the twice a week newsletter where I typically write off the cuff, I’m going to take my time to write thought-provoking pieces that will go through multiple rounds of feedback and edits. Thanks as always for following along!

Last Monday night, as I was scrolling Twitter, my heart started to race.

I read a Tweet that felt like it was speaking directly to me, but in reality, it was sent to thousands of people across the internet. I wanted to respond but I was unsure. So I ignored it and moved on.

The next morning, I was still thinking about that tweet. I checked Twitter to see it getting more traction with several comments from other high profile people.

I mulled over it all morning. At my 11 AM call with my weekly accountability group, I asked for their advice. The answer was clear: I had nothing to lose.

10 minutes later, I responded to the tweet.

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Now for some background.

In June, I attended Craft + Commerce, a conference in Boise for creators. Here’s a quick excerpt from my takeaways immediately following the event:

Before that workshop, I had never heard of Barrett. Previously, he helped scale ConvertKit from $3M to $30M in revenue as the COO. Now, he is an executive coach for creators making $1M+ in revenue and hosts a podcast called Great Work. I was impressed by his ability to survey the room, provide relatable and funny anecdotes, and connect with the room of 50 people. I took 5 pages of notes and at one point wrote “I want to hire this guy”.

After the event, I sent Barrett a quick email saying that while I left that room feeling like I didn’t belong, I could see myself belonging in the near future. I thanked him for a great session and said I’d love to potentially work together in the future. He got back to me a few weeks later with some thoughtful words of encouragement and an offer for me to reach out if there was anything he could help me with.

In the months since, I’ve listened to most of his podcast episodes (even writing about one) and have passively followed him on Twitter. I really vibed with his approach on business and life.

So when Barrett tweeted that a spot opened up on his annual fishing trip with a bunch of entrepreneurial and impact oriented guys, it felt like a rare opportunity to once again “get in a room” that would make me feel uncomfortable.

Since I don’t have a blue checkmark, Twitter didn’t even let me DM Barrett. But at the end of his workshop, he gave his cell phone number to everyone in the room. I dug through my notes from the conference and sent him a text.

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After sending the text, I went on with my day and tried not to think about it.

But it was all I could think about.

Did someone else already take the spot? Would he remember our email exchange? Would he even want someone like me on the trip?

My phone was on do not disturb, but I couldn’t resist constantly checking to see if a new text popped up.

3 hours later, a text from Barrett came in. But not just any text. A 9 minute voice memo.

What the hell did this guy have to say for 9 minutes!?

I finished up the work I was in the middle of, put on my sneakers, and went outside for a walk. I put my AirPods in, took a deep breath, and hit play on the voice memo.

He told me how the guys on the trip were entrepreneurial and career driven. They didn’t have flashy or intense personalities but were thoughtful and down to earth guys who quietly built successful businesses and careers. The age range was 35 - 47 and most were committed dads, but those weren’t requirements. He talked through the specifics of the 3-day itinerary drifting down 30 miles of the Deschutes River in Oregon with no cell service and getting to fish for Steelhead Trout in some of the best fly fishing conditions in the country. He gave me background on each of the guys attending and ended with “Let me know if you’d like to join!”

Holy shit, this was real.

I spent the last year designing my life to take advantage of an opportunity like this. My work is flexible to allow me to take 3 days off at any time. I can hop on a plane in 4 days’ notice and fly anywhere in the world. I’ve built the confidence to spend 3 days with people I have never met. I developed a love for adventure hiking in Patagonia and climbing Mt. Kilimanjaro so getting to learn fly fishing for the first time was exciting.

But then the rational side of the brain started to kick in

• Should I really go on another trip? I just got back from Kilimanjaro and was looking forward to settling into Austin.

• What could I possibly contribute to this group who are already wiser, more experienced, and more successful?

• Is this worth dropping $3,000 for four days?

• What if these guys are all crazy and I am stuck in the middle of nowhere with a bunch of people I don’t know?

So, in that moment of doubt, I called upon my board of directors. The people in my life who I can run my crazy ideas by and get objective advice from. It only took a few minutes of explaining the situation to two of these friends to realize I already knew what the right answer was. However, it did feel good to get the validation and encouragement to go for it.

Knowing the right answer is one thing, but taking action on it is another.

It was already Wednesday night and the trip started on Sunday. I didn’t have much time to think this over. The tight timeline actually helped me not overthink the situation and just go for it.

At around 6:45 PM, I sent a voice memo back to Barrett thanking him for the response and all the details. I gave him a quick rundown of my journey from corporate to entrepreneurship and my love of adventure and meeting new people. I told him I’d love to join the trip and to let me know if he thought I would be a good fit.

By 10:30 PM as I was getting ready for bed, I still hadn’t heard from Barrett. Maybe I was too late or he was looking for someone more established. I went to sleep cautiously optimistic but proud either way that I tried.

The next morning I woke up to a text “Let’s do it Andrew! Book the flight”.

Holy shit, this was happening.

Final Thoughts

I heard this quote from Will Smith that has stuck with me for the past 2 years:

I’ve adopted this mentality of running towards fear. When something feels scary, there’s a reason for it. If it’s actually life threatening danger, that’s different. But if the fear is just uncertainty or discomfort then those are the things that will help me grow.

This is what pushed me to say yes. I knew that leaning into this unknown would help me become a better person in some way. And the only way to find out how was to hop on that plane. So that’s exactly what I did.

Stay tuned for Part 2 to hear more about 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