The worst possible week to sign up for an ultramarathon

The same week I found out I was being promoted to VP, I got off the waitlist for a 65-mile ultramarathon.

The Never Summer 100K is a popular race I didn’t think I’d get into. I also didn’t think I’d get promoted to VP of Marketing. Apparently, the universe has a sense of humor.

I almost held off on the race. The math didn't add up. I was stepping into my first VP role mid-quarter, inheriting a hiring process, managing a team through a leadership transition, and suddenly responsible for a board presentation I hadn't been planning for a week prior. Adding eight-plus hours of training a week felt almost irresponsible.

Am I setting myself up for failure and misery?

Another thought popped up: people do this. Leaders have families. They have lives. They run very long races in the mountains. You don’t have to trade everything you love for work.

So I said f*** it. And then yes to both. 

Training for this thing has, ironically, become one of the main ways I’m building in time for “slowing down” and reflecting on all of the other fast-paced changes from my first months as VP.

Moving fast and thinking slow

I’ve had to be deliberate about finding places where I can ease the mental load. Most of the time when I’m running, I’m honestly trying not to think. I throw on my music and try to melt into the flow of my steps. But ideas about work and life come anyway. 

A conversation I need to prep for surfaces. A pitch I've been rolling around clicks into place. I suddenly know exactly how I'm going to frame something for the board. I think about texts I need to respond to and whats going on with my family. 

Running wrangles my mind into a more relaxed, open state. It also tempers the emotions of the day enough to help me look more reasonably at hard situations. 

I journal on the regular too, as you learned from my retelling of how I spent the night I got promoted. Journaling, even the act of writing this newsletter, does something different. Where the miles give me subconscious bandwidth, putting pen to paper gives me a place to consciously examine things. I've been writing for years, but this season it's become more purposeful. There's a lot to work through. New relationships, early mistakes, the ongoing adjustment of being the person in the room who leads rather than the person in the room who contributes. Getting it down helps me see it more clearly than I can when it's just noise in my head.

Moving too fast and thinking slow

Having a marketing team that’s honest with me has also made it possible for me to pull back and change course. Specifically on something that I messed up in my first few weeks. 

When you're a contributor with strong opinions, that energy reads as enthusiasm. When you're the leader of a team, that same energy can read as "I don't trust what you're doing." I was sharing thoughts and spewing opinions in ways I’d hoped would be conversation starters, but landed as directives. It understandably rubbed some people the wrong way.

What I learned: intent has to be clear. 

I come in with ideas because I want pushback; because the friction is what makes the idea better. But if I don’t make that clear, it sounds like I’m just telling people what to do. So now I just say it. When I took the SDR team under marketing, I told them straight up: I come in hot sometimes. But I’m bringing ideas to the table in hopes that they start a discussion, not end it. Push back. That's what I'm hoping for.

It's a small thing but it's helped a lot.

Why all of this matters

I'm a thinker. Always have been. 

Mark flagged it explicitly in our transition conversations. He knew me well enough to say, "Most people need to get to 80% before they act; for you, it's more like 60 or 70." 

I can hold onto the last 20% of something long past when I should have shipped it. I will stew on conversations from earlier in the week. I’m quite literally still haunted by things I said in high school.

That personality type has served me. It's made me better at the strategic and creative work of product marketing. It's made me a more thoughtful communicator. But stepping into leadership introduced a new wrinkle to my overthinking tendencies that I didn't fully anticipate: Decisiveness is mandatory, but every conversation has weight. 

A casual Slack message to a co-founder is a leadership interaction. A one-on-one with an SDR on my team can motivate them or send them spiraling. I immediately had a few misses; moments where I could feel that gap between my intent and my impact. Those stung. And for someone wired the way I am, that awareness of the consequences can become its own kind of paralysis.

I’m treating decisiveness like my running though, building the muscle through consistent training day by day. But managing the instant replay in my head, not letting it derail me, is active work I also have to do.

Where I’m at right now

I'm approaching two months into VP life. My daily schedule is still wrecked. But the initial chaos is starting to settle down and my first full quarter in-seat is beginning. I’m happy with the moves made and where the team is at going into May. 

Stepping into this VP role has evoked my natural inclinations to mentor and motivate. And the trait I was most worried about (my deep introspection and the tendency to stew) can become one of my leadership strengths if I manage it right.

If you're in a new or growing leadership role and you're wired like me, the move isn't to try and become a different person. I initially thought I’d need to change, but our co-founders made it clear that they were excited about me in this position, and what I bring to the table. That includes my thoughtfulness and over-thinking tendencies. So the move is to adjust and grow in the areas I need to, like decisiveness, while making space for the outlets I need to stay sane. For me, thats something physical like running. Something reflective like journaling. For you, it might be something else. Just give your brain somewhere to process that isn't a Slack thread or a meeting. Something that's yours, that doesn't produce an output, and that you protect even when things get busy. Especially when things get busy.

Would love to hear what that something is for you. Talk soon.

—Al

3 things I’m digging this week:

• We A/B tested proof that actually drives conversion — I’ll be joining Casey Hill from DoWhatWorks on May 28th to talk about how customer evidence can drive results on your website. Excited to share some interesting findings you can use right now.

• Noah Kahan’s new album — Yeah, yeah. Me and everyone else I know. But man is it a great album.

• AEO strategy overview — A good primer to AEO strategy from our friend Brendan Hufford. We’re investing in AEO and I’m very curious to see how it pays off this year (it does just feel like SEO 2.0 to me though).

🏔️ Highline 2026 applications are open

You, 100 other B2B marketing leaders who get it, and 3 days in Jackson Hole.

Highline 2026 is on. If you’re a Director+ marketing leader who wants to join us in the Tetons from August 3-5, apply right here by May 15th. Spots are filling up quick.

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