long-term optimistic, short-term clusterf*ck

Good morning Predictable Revenue community,

Book update - I’m waiting on the copy-editing team to come back with harsh criticism of my speling and gramer. Then they’ll send me revisions and I guess get to decide if I agree with them or not? It feels like getting a test graded but the teacher’s on your payroll so you can decide if you get an A or not… I’m not great at sitting still so I’ve been reaching out to friends and colleagues for reviews of the book, here’s one that rolled in today:

Getting Caught in Neutral

I was talking to a friend this week about his startup and asked how things were going. His answer struck me right between the eyes: “Long-term optimistic, short-term clusterf*ck.” I couldn’t have summed up my own year any better.

I started January feeling oddly stuck in neutral. On paper, we had all the moving parts: marketing and sales teams reporting to me, pipeline volume that looked steady, and a sales team closing deals at a consistent (could always be better) rate. But the leads weren’t the right quality—lots of Gmail addresses and ghosts who vanished. January’s numbers took a hit, and February wasn’t looking great either.

Despite understanding the seriousness of the situation, I spent too many days paralyzed by competing priorities. It wasn’t that I lacked ideas; I just couldn’t figure out which fire to put out first. Meanwhile, I found myself hitting refresh on my inbox, half-wishing a miracle deal would appear and solve all my problems. It didn’t, and eventually I had to face that no one but me was going to fix this.

I’ve been here before, not often, but let’s say it’s familiar territory. I’d see the oncoming train and almost feel tempted to just let it run me over, letting everything go. Not in a physical / you need to worry about Collin way—but in that “maybe I’m done with this company” sort of way. Yet, my entrepreneur friends always jokingly called me “the cockroach,” because no matter what happens, you just can’t kill me. Over the years, I’ve had cofounders back out, huge deals evaporate, my site crash with no CTO in sight, and somehow I always got back up.

Rediscovering My Why

Getting unstuck this time began with an honest look at what I truly cared about. I realized I had lost my excitement for building sales development teams. It was something people wanted, so I went with it, but it never lit a fire in me. Don’t get me wrong, I can still get fired up about Clay tables and all the cool stuff you can do with the tool, but it’s all the mundane stuff that was killing me. What I do care about is helping founders. Once I decided to focus on that again, everything shifted. Suddenly, I wasn’t stuck in place because I cared. Even though the fires around me still needed putting out, I had a renewed sense of energy for the work.

If you’re not a reader, here’s a little context: over the last 13 years, I’ve launched a CRM that attracted only one paying customer, burned my savings, pivoted to email prospecting services, spun up a sales engagement tool that quickly hit seven figures in revenue and then just as quickly churned out, and even toyed with closing shop before the pandemic. Through it all, I stuck around out of loyalty to my team and an inability to quit. After all that, I’m still here—my company is hitting its 13th birthday this weekend, and I’m still the cockroach, alive and kicking.

How I Got Out of Neutral

Once I decided to shift my company’s focus back toward helping founders, I felt a sense of responsibility to back that decision with real, day-to-day tactics. Weekly planning alone wasn’t cutting it; I needed more immediate structure.

At just the right moment, I stumbled across two reminders. The first was about the Ivy Lee Method: at the end of each work day, you write down the six most important tasks you need to accomplish the next day, then work through them in order of importance. I was reintroduced to this simple system through David Manner’s startup newsletter. I’d used it years ago when I was a salesperson and was stuck with Microsoft’s Dynamics Navision as my “CRM”. There wasn’t much CRM really in there so my spiral-bound notebook + the Ivy method was my go-to.

The second reminder came from a friend who nudged me to revisit Tim Ferriss’s podcast episode featuring James Clear, author of Atomic Habits. The episode delves into the power of building habits and focusing on process rather than perfection. Both these reminders helped me realize I was letting big, undefined tasks paralyze me. Splitting my workload into precise, prioritized steps—before the next day began—meant I never had to show up in the morning wondering where to start.

Making the Most of My Time (and Sanity)

As I worked on my post-it one night, I was scanning my inbox and—you’ll never believe this—got completely sidetracked by a newsletter subject line that I just had to click on. It read: “Why You’re Always Busy but Never Productive (and How to Fix It).” The post, on Nir’s blog but written by Sahil Bloom, hit me right between the eyes. In a nutshell, he explains that being busy can actually be a form of procrastination—an easy way to fill our days with tasks that feel like work but don’t really move the needle. He clarifies the difference between traction and distraction, arguing that if we don’t intentionally plan our day, our day will plan itself (usually in the form of shallow, low-impact work).

Sahil also proposed splitting your professional time four ways, Management, Creation, Consumption, and Ideation. It reminded me of Paul Graham’s Maker Schedule / Manager schedule with time blocks added in for educating yourself (consumption) and long term planning (ideation). The common thread: the importance of intentionally carving out space for deep, meaningful work. Multitasking, constant Slack notifications, and scattered scheduling were all killing my focus. By blocking two-to-three-hour stretches for higher-level strategic tasks, then confining my email and administrative check-ins to specific windows, I regained a sense of control.

Parting Thoughts

I’m still battling day-to-day chaos but that’s nothing new. The short-term mess doesn’t disappear just because you found a neat trick, but these methods help turn frustration into forward motion. If you ever find yourself refreshing your inbox, hoping a miracle will fix your problems, stop and ask: “What would move the needle the most tomorrow morning?” Write that down, and commit to doing it first.

The only way out is to fight through it. Whenever I’m feeling stressed, it’s almost always because I don’t feel like I’m doing enough about the problem. Knowing that is key to reducing my stress about revenue. Any time that anxiety creeps in, I make sure I prioritize something that will contribute to pipeline for the next day. In other words, I shift my focus to the most direct, practical action I can take.

Sometimes the simplest approaches—like deciding your next day’s priorities the night before—are what bring you back to life. If you’ve been feeling stuck in neutral, I hope this helps you shift into first. And remember: cockroaches can survive just about anything.

Okay, post-it note time, catch you next week.

Collin

PS - A friend recommended ChatGPT Pro last week so I signed up. If you’re researching a new market or trying to find a tool to solve a problem, it’s worth the investment. It’s like having a somewhat competent recent grad working for you. If you give it good instructions, you’ll probably get something useful from it. And like a recent grad, you probably want to double check it’s analysis. I’ve noticed I’m starting to “search” with it more regularly. If this keeps getting better, I’m not sure what’s going to happen to SEO.  

PPS - here are the posts and podcast that provided inspiration for this post:

• Nir Eyal’s blog “Busy but Not Productive” (feat. Sahil Bloom)

• Paul Graham’s “Maker’s Schedule, Manager’s Schedule”

• The Ivy Lee Method by Mayo Oshin

• Tim Ferris & James Clear Podcast

PPPS - I guess it’s valentine’s day so here you go 🌷