Yes, yes. I’m publishing the newsletter 12 hours late. My sincere apologies to those of you keeping track. Life tends to get in the way at times, and yesterday was one of those days. I decided to prepare for our new house move, get a workout in, throw the football in the front yard, and attend the Colts game instead of pushing to publish this last night. 

That’s life, but here we are, and it’s a good one. :) 

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“These inner battles have actually trained you for this very moment. You are strong because you are imperfect. You are wise because you have doubts.”

And here we are again… on another plane, writing from 20,000 feet on a flight from Paris to Atlanta. Nine hours was enough time to catch up on work. Still, I also had the chance to rewatch The Darkest Hour, which is about Churchill’s first days as Prime Minister, with Dunkirk collapsing, Halifax and Chamberlain pushing for peace talks, and the U.S. hesitating to support Britain in the war. It’s craziness, and it makes our “board meeting anxiety” look laughable in comparison.

There’s a scene I’d missed before: Clementine (Kristin Scott Thomas) tells Winston (Gary Oldman) that line above. I had to pause the movie, pull out my laptop to write. It’s the perfect example of why doubt and imperfection (or the head trash we will discuss below) are the raw materials of authentic leadership. 

“These inner battles have actually trained you for this very moment. You are strong because you are imperfect. You are wise because you have doubts.”

So good, and that’s the thread for this week. Below, I’m sharing a practical guide for dealing with head trash (all the imposter stories that live in our heads as we go through this life). It’s the stuff I use: keeping receipts so evidence beats emotion, “share before ready” to shrink the vacuum, a three-line update to over-communicate without performative decks, a lightweight cadence to over-communicate, and a simple 90-second ritual to reset before big moments. I also walk through how to build a small peer network that tells you the truth.

And because strength isn’t just for work, I’m linking a new Revenue Diaries conversation with Brendan Hufford. It’s on ambition, repair, and raising strong kids. In a nutshell, it’s all about being strong so you can take care of other people. It’s the same antidote to head trash (evidence, repetition, service) just applied at home.

Here’s to our imperfect battles in our heads,

♥️ kyle

The Complete Guide to Dealing with Your Damn Head Trash

Earlier this week, I spoke with a future marketing leader who said her imposter syndrome is debilitating.

My response: “Yep. I deal with it almost daily. I call it head trash. I don’t ever fully believe I’m doing enough or the right thing.”

I’ve learned the hard way that the people you least expect (the strong operators, the high-functioning leaders, the ones their teams respect) feel this too. It’s not a glitch in your personality; it’s indicative of doing real work in public.

And the public is louder. Thanks to our wonderful feeds, pumping an endless stream of other people winning (even the blowhards). Meanwhile, many of us continue to work from home in isolation, which creates a head trash breeding ground: you get less feedback, fewer signals that you are working on the right things, and even less support. And in this head trash breeding ground, your brain fills the gap with worst-case stories, or at least it does for me. 

I’ve never completely learned how to vanquish my head trash on command. But through therapy and my own research, I’ve learned how to quiet the smelly trash in my head. 

Competence isn’t omniscience: Seniority raises the quality of your questions; it doesn’t eliminate them. Experts navigate ambiguity and make decisions in the face of uncertainty.

Gobbly-gook. Here’s what that looks like in real life: As a CMO, I get this all the time: “What will this launch add to this quarter's pipeline?” I don’t ever have the perfect number, but I do have better questions to help answer (not real numbers, just an example):

• Assumptions: win rate = 18–22%, ASP = $48–55k, reach = 200 target accounts.

• Plan: ship a 70% version to a controlled list, instrument first-touch → opp creation, 14-day read.

• Guardrails: if CAC payback > 24 months or demo→opp < 10%, we pivot message or pause spend.

• Next step: enable sales with a 1-pager, launch two creative variants, review signals next Friday.

Seniority doesn’t erase uncertainty; it upgrades the questions you ask and the experiments you run so you can make the call without pretending to know everything, because you don’t.

Imposter feelings are data, not destiny: Sometimes they point to a skill gap to close. Sometimes they’re just the tax you pay for growth. Treat the feeling like a signal to investigate, not an order to obey.

Example: Just because you f*ck up in a meeting or you “forget” a number doesn’t mean you aren’t good at your job. I’ve had to spend hours working on my presentation skills and how I present information to regain confidence. It’s not that you aren’t good at your job; it’s just the pain you have to go through to grow. 

Evidence over emotion: Feelings are inputs, not verdicts. Ask: If I looked only at evidence from the last two weeks, what would I conclude about my performance? Keep the receipts for your wins and losses! If you do your job, you will have more wins.

I keep a living/working document of wins, resolved issues, lessons learned, and kind notes. I try to review it before any big meetings or decisions. Having evidence of your accomplishments will help quiet the noise. 

From proving to improving: Swap “prove I belong” for “learn one thing per iteration.” That’s a game you can actually win.

Okay, I know I promised a guide or playbook to deal with all this bullshit in your head. Here’s a starting point, because life is messy, and I’m never going to be able to give you the complete guide… this is what helps me on the day-to-day.

1) Write your receipts. Keep a folder on your desktop or phone of: 

• Wins and resolved issues

• Lessons learned

• Kind notes/testimonials

Review it before big moments. It’s your Swipe File to help quiet the head trash. Here’s where I started:  

• This week I shipped: ___

• A problem I solved: ___

• A thing I learned: ___

• Feedback worth keeping: ___

Start a project folder in GPT called “Dealing with the HT” and spend some time at the end of each week chatting through the different learnings and wins. It’s a great way to keep track of what works and what doesn’t.

2) Raise the right standard. “Zero ambiguity, zero errors” is a fantasy. Try Share Before Ready: circulate drafts at 70% with a clear ask (“gut check on narrative,” “holes you see”). You don’t always need to have a finished project to review. Get feedback sooner and more often. You’ll move faster and trust yourself more.

3) Define “done.” Write 3–5 observable behaviors that define success in your role. If you hit them this week, you’re not faking it. And if you don’t, you are still probably in the clear, butyou need to do the work. :) 

Example:

• Communicated priorities and trade-offs to stakeholders for quarter or annual budget planning

• Shipped one customer-facing asset that supports the sales team on deal advancement 

• Ran a post-mortem on a campaign and captured improvements

4) Perfection is a delaying tactic, and over-communicating builds trust. The longer I stall or tinker on a decision or project, the more the head trash festers and grows. The fix is boring and fast: narrate the work while it’s in flight. I try to use it three times to help improve:

1. Here’s what I know: the facts, current state.

2. Here’s what I’m testing: the hypothesis or next move.

3. Here’s the risk & mitigation: what could go wrong and the guardrail.

When you do this, you shrink the calibration vacuum, invite helpful feedback, and stop pretending you have it all figured out.

And because I’m trying to be as helpful as possible, here are a couple of examples: 

Slack update (real-time, 30 seconds):

• What I know: Traffic is up on the new pricing page; demo requests +9% WoW from paid search.

• What I’m testing: Two headline variants—ROI vs. time-to-value—running a 10-day A/B.

• Risk & mitigation: If demo→opp dips below 12%, we revert copy and cap spend to brand until we regroup.

Quick meeting talk-track (under a minute):

• Know: “We have 200 tier-1 accounts; 47 engaged in the last 14 days.”

• Testing: “Launching a 3-email sequence + SDR bump to those 47 this week.”

• Risk & mitigation: “If reply rate <2%, we’ll swap the CTA to a 3-minute product tour and tighten targeting.”

That’s it. You don’t need a lengthy memo of ten slides in our favorite Google Slides template. Just tell people where you are, what you’re trying, and how you’ll avoid failure or downside. But the most important thing: It reduces posturing because you’ve already acknowledged uncertainty and set the rules for how you’ll handle it.

If you want to push this further, make it a lightweight cadence:

• Mondays: Post a three-line update on your biggest bet.

• Midweek: Share one interim signal (good or bad) and confirm the next test.

• Fridays: Close the loop. Did it work? What’s Next? 

5) Build a peer network (not just a feedback loop). I’ve found my head trash only grows smellier when it’s left to fester in isolation. And I’ve found isolation is easily solved by building a small bench of trusted peers who see similar problems and will tell you the truth. 

Pavilion has also been my go-to peer network. You can choose between posting a thought or question in their community of thousands of GTM leaders or joining their peer networks. If you don’t want to join a group like Pavilion, it’s completely up to you to build your own network, here’s what I’ve done in the past: 

• Pick 4–6 peers at a similar scope (not direct competitors if that limits candor).

• Set rules up front: confidentiality, no posturing, practical over performative.

• Meet biweekly for 45 minutes, same time, same link. Calendar > intention.

  • Round-robin (10 min): one win, one stuck, one signal you’re watching.

  • Hot seat (25 min): one person goes deep: context → question → options. Group gives evidence-backed takes, intros, or templates.

  • Commit (10 min): each person states one next step they’ll report back on.

• Outside the meeting

  • Create a signal channel (WhatsApp/Slack). Share receipts, drafts, quick polls.

  • Keep a shared vault in Google Drive: playbooks, vendor notes, interview Qs.

  • Do monthly 1:1 check-ins with one peer on sensitive topics.

Peers give you calibration your org can’t. Build the room, set the rules, and let honest operators turn down the volume on the head trash.

8) Don’t doomscroll. DON’T DO IT! Put social apps on your laptop only, not your phone. Time-box them to one 15-minute window. Replace idle scrolling with a walk or two minutes of box breathing.

And last but not least, this has been the best formula for deodorizing the smelly, festering head trash (maybe I should back off on the trash analogy). It only takes 90 seconds, but you can shorten it; it’s the thought that counts. 

The 90-Second Ritual (thanks, therapy)

• 0:00–0:30 — Name the fear. One sentence. No drama. “I’m afraid this launch will flop and I’ll look incompetent.”

• 0:30–1:00 — Pull three receipts. Evidence that cuts against it. “We’ve hit our last three deadlines, customers validated the message, and sales asked for this.”

• 1:00–1:30 — Choose the smallest next step. “Send the draft brief to sales for a 24-hour read.” Then do it.

Confidence isn’t something that should be fleeting. It isn’t a random mood. It’s a by-product of practice and constantly striving to be better. 

Head trash will always be there. It’s part of being human, unless you are the 2% of absolute psychos, and if you are, you probably aren’t reading this newsletter anyway.

Gather the evidence, share it with your team, and move forward. When you are moving, the head trash becomes less smelly and more useful (biodegradable FTW). If you practice and you keep track of the lessons, share them.

Let’s give each other better calibration than the feed ever will.

On Ambition, Repair, and Raising Strong Kids

Listen to the full episode with Brendan Hufford.

I brought Brendan Hufford on the podcast to talk about everything other than work: childhood, parenting four boys, getting punched in the face in an MMA gym, CrossFit timing vs. bedtime, and why “be strong” is about service, not ego. 

I love Brendan and I loved this conversation because it’s as real as it gets. My favorite part is when Brendan tells a story about his 7-year-old playing baseball and catching one game, coming home obsessed, and sleeping in his new catcher’s mask. It’s cute but not the main point: Then he pivots:

“Not the sports and the athletics are the thing. The thing is, I want to give them values that can’t be taken away. We talk about this a lot:  We want to be physically strong so we can take care of other people. We’re creative. We’re hardworking. I repeat it until they say, ‘That’s who I am.’”

That’s the clip I’m sharing with this entry. It’s worth watching.

The chip and where it came from

Brendan grew up moving a lot, in a single-parent home, “looking trips” to toy stores because buying wasn’t an option. He took his boys back to his old neighborhood in upstate New York… multiple houses boarded up or burned out.

Someone once called him “a hustle bro drunk on his own Kool-Aid.” His response: you might not be wrong about the intensity, but let’s talk about why the intensity exists. That context matters. It also explains a lot of his drive and the calibration work he’s doing now as a dad and coach.

But that intensity can also be a liability. He had a sideline reckoning: after a rough soccer game where Brendan was super hard on his son, he told Brendan, “I don’t want to be that good at this. It’s not that important to me.” Brendan backed off. Not every kid wants reps like you do. Not every kid needs your standard. The goal is joy and growth, not a carbon copy of your drive and energy. Your kid is a different human.

Strong, but not brittle

There’s a thread in Brendan’s story: strength without posturing.

• He found MMA in college, walked into a gym, got blasted in the face on day one and kept training.

• He never fought publicly as a teacher/assistant principal (two first days of school with a black eye will change your mind), but he trained hard.

• Today it’s CrossFit because jiu-jitsu class times conflict with bedtime—and he refuses to miss that trade.

That line says more about “priority” than most leadership books.

Repair > performance

We did a quick-fire round: his favorite “dad win” lately? “Saying I’m sorry.”

Simple, not easy. Especially for boys who need a model for healthy masculinity… physically strong and resilient, and also quick to own it when you blow it. Parenting is mostly repair.

Nature, nurture, and letting your kid be your teacher

As his boys get older, he’s realizing how different they are despite similar values and parenting. The oldest is introspective and challenges Brendan’s stated beliefs in real life. Example: painting his nails, punk jean jacket from Goodwill, patches. It forced Brendan to decide whether his “I support self-expression” stance holds up when it’s his kid walking into school. Growth on both sides.

Trading rage fuel for better fuel

This might be my favorite arc. The chip that powered early ambition (the anger, the resentment) works, but it breaks you. Red Rising (yes, the sci-fi series) helped him swap in something healthier. He taps the necklaces he wears and thinks of his kids before heavy lifts. “Be strong to take care of other people.” That’s fuel that doesn’t hollow you out.

Writing as therapy, and how to actually start

Clear writing is clear thinking. He wrote daily for years—letters to his sons on Medium, notes from podcasts, everything. Two simple tactics that stuck:

• Lower the bar to start: write a page, even in Apple’s native Journal app with a photo and a few lines from the day.

• Make it bite-sized and consistent: if “floss one tooth” gets you to floss, “write one paragraph” gets you to write.

Most of us in ambitious roles carry a version of Brendan’s chip. The work is learning when it helps and when it harms, and then choosing better fuel. Repetition builds identity. Identity drives behavior. In teams. In families. In ourselves.

If this resonated, forward it to the most intense parent you know. They’ll get it.

Listen to the full episode with Brendan Hufford.