The year is 2015.
The iPhone 6 drops. The latest Jurassic Park reboot edges the latest Star Wars reboot for the highest-grossing film of the year. And you remember Uptown Funk, right?
It’s the year I hit the publish button on my first blog post, Joyfear. The year I was included in one of Oregon’s largest layoffs in 10+ years. And the year I took a flying leap off the ledge of predictability and into an ocean of WTF am I doing.
That first post kicked off a job search campaign that would include a return to college at 40, two unpaid internships, a year of freelancing, and my music video resumé called I Got Skills (at a time when that kind of content was still a novelty). I even got a nice write-up on the local Portland job board, Mac’s List.
Ten years later, the skills are paying the bills.
Going back to school as an adult was such a gift. Working for OEN (Oregon Entrepreneurs Network), a non-profit supporting local entrepreneurs, was foundational and exciting. And I’ve had an absolute blast over the last five years helping AI personalization provider Rebuy grow from a scrappy 8-person startup into a scaling force in B2B e-commerce with two funding rounds in the bag and over 120 full-time employees.
This post is a list of 10 lessons I’ve learned (or relearned) in the 10 years since I published Joyfear.
The world has changed drastically over the last 10 years. It was the ‘before times’ then. And now? Remote work, AI, and once again, the latest reboot of Jurassic Park. Some things change. Some things stay the same.
If we haven’t met: Hey! I’m Miles. I’m a marketer, musician, and creative person who loves tacos.
If we’ve met before, thanks for being part of this ride.
News flash: AI is a blazing-fast copy editor. So I used it to help me edit and revise this post. I’m evolving my writing process these days, and I’ve been leaning on voice-to-text more and more. So my process here was: dictate my notes and ideas into an LLM (ChatGPT 4o), use it to draft an outline, sloppily write more than I need to, then use the LLM to refine, condense, and sharpen what you’re reading now. Pretty neat, huh? Super efficient, too.
Okay, on to the fun part.
Lesson 1: The biggest risk is staying put
Comfort can be a trap. And Resistance is to blame. Resistance is that inner voice that tries to convince you to just relax and stay put. It can be very persuasive, too. “You don’t need to do that important right now,” it says. The next thing you know, 10 years have gone by and you’re no closer to your goal. The good news is, you can conquer Resistance. As Stephen Pressfield, author of The War of Art, says, “the more important to your soul’s growth, the stronger the Resistance will be.” So do the things you’re most afraid to do, because that’s Resistance telling you where your greatest fulfillment lies.
Lesson 2: Be the scientist
“Without a good question, a good answer has no place to go.” – Clayton Christiansen
Most people default to telling instead of asking. And sometimes that’s the best move. But asking the right question(s), like the 5 Whys or The Coaching Habit’s opening three-question power combo, usually gets you further in my experience. I like how Adam Grant frames it as the choice between playing the role of the scientist versus the prosecutor. Prosecutors defend their ideas at all costs. Instead, approach your work and life like a scientist: test, learn, adjust. In other words, stay curious, my friends.
Lesson 3: Turn your knowledge into systems others can build on
I learned this one out of the gate at OEN, where I built systems to track two newsletters, social media content for 4+ platforms, and managed all the content and communications for the 50+ events, workshops, and networking events we put on each year. At Rebuy, I interviewed my team and cross-functional stakeholders (Sales, Partnerships, Ops, and more) to help me build a content operating system (the “Marketing Hub”) that streamlines team collaboration. Now the team owns it, and some have customized it to improve it further. The message here is: Build frameworks and templates and systems that make your team (and your future self) better.
Lesson 4: Give kudos
Remember, you’re in the people business. Recognizing your people (direct reports, peers, bosses, executives) is the mark of a good leader. And praising your colleague does not dim your light. At Rebuy, we have a system anyone can use to give shoutouts to anyone else in the org. There are plenty of benefits to giving kudos for a job well done. Plus, it’s just good karma. So be generous with your kudos and employee recognition.
Lesson 5: Play the long game
You will be underestimated, under-appreciated, undercut, overlooked, passed over, ridiculed, written off, dismissed, left out, baited, slighted, railroaded, thrown under the bus, and left for dead. And when this happens to you, do this: deliver value anyway. All the time. As often as you can. Because you’re on a mission, and you’re playing the long game. The value you deliver against all odds will generate compounding interest over time.
Lesson 6: The way out of imposter syndrome is through execution (and patience)
Control what you can control.
Imposter syndrome. I felt it for a minute there. And by a minute, I mean several months, and probably more like a year if I think about. One big step forward was joining a community of marketers and speaking with a couple of the mentors there. (Shoutout to Peak Community.) Another effective strategy for me was being patient, and notching a win or two. Pick a project you know will add value (by vetting with your team) and chase it like my border-aussie Watsen chases squirrels — with reckless abandon.
Sahil Bloom illustrates the concept nicely with what he calls the Clarity Curve. In his post, Bloom quotes Rumi who said, “As you start to walk on the way, the way appears.” Once I delivered something valuable that I was truly proud of, my confidence grew. And I could feel the spell begin to lift.
Image: Sahil Bloom’s Clarity Curve.
Lesson 7: Pass the mic
Here’s the snappy AI-generated hook I can’t bring myself to delete: “If your team feels heard, they’ll be more invested. If your customers feel heard, they’ll buy again. And if your cross-functional partners feel heard, they’ll show up.” I mean, it’s not wrong.
One of the most overlooked levers in growth is listening. I’m talking about structured systems that make listening a habit. That’s what we’ve tried to do at Rebuy with the GTM Sync initiative. It’s a quarterly cross-functional meeting focused entirely on our customers: what they’re asking for, what they’re struggling with, and how we can deliver more valuable content across every touchpoint. Reps from almost every department join. We document everything. The ideas we gather become fuel for partnerships, content, sales, and support. It’s a good time.
Lesson 8: Let the best ideas win
The best ideas don’t always come from the loudest voice or the highest title. At Rebuy, we use org-wide surveys, creative brainstorms, and team voting to push our best ideas forward. It’s so important to give good ideas the oxygen they need. Letting ideas compete on their own merit creates better outcomes (and stronger teams). Want to double-click on that? Sales and customer success expert Stefan Willis shared a killer list of tactics to build a culture that lets the best ideas win.
Lesson 9: Know when to step up, and when to step back
You don’t need to have a take on everything. You don’t need to fight for airtime to be effective. And you don’t need to chase validation. Personally, I tend to listen more in meetings. I try to save my energy for the things that actually matter. Like, when an idea’s worth defending or we’re about to make a call we can’t easily reverse. If I’m facilitating the meeting, I want to hear from everyone. The bottom line here is, pick your battles. Use silence strategically. And speak with the right balance of curiosity and conviction when the moment calls for it.
Lesson 10: Tell good stories
Whether you’re writing persuasive copy for a new product page, looking to land your next dream job, or reading The Princess Bride to your little one, getting good at telling a story can solve all kinds of problems. When I look back on the last 10 years, my best work has involved storytelling. For my job search, it was the I Got Skills campaign and the Mac’s List write-up, telling the story of a job seeker doing something bold and creative to land a dream job. For OEN, it was telling the story of local entrepreneurs making an impact. For Rebuy, it’s been interviewing customers and crafting stories that get noticed. So go forth and be the teller of tales, the weaver of dreams. Because we all love a good story. And, besides, storytellers are in demand.
Ten years later, and I’m still figuring things out. Only now I’ve got a few more stories, a few more scars, and a lot more grey hair. Thanks for reading. If anything here resonated, I’d love to hear your story, too.