That feeling when you know you could've done better
And what I'm committing to in 2026
I could’ve executed better on that…
That was what my inner voice kept saying to me when reflecting back on the key initiatives I put in place last year.
This is the dark side of having incredibly high expectations and standards. It drives success (because that’s the only result we’ll settle for), but it also means rarely being at peace with how it played out. We take on things we know we can do well…and avoid/delegate the things we don’t do well.
We don’t celebrate the parts that went well (the expectation is success, so why wouldn’t XYZ have gone well?) and obsess over what didn’t go well, what could’ve should’ve been done better. And as I look back at last year while preparing for the year ahead, I wanted to understand why I kept having this feeling and how I can finally get a better wrangle on it.
Which has led to my 2026 “work resolution.” Just 1, and a very simple 1 on paper, but I know will be the hardest resolution I’ve ever set for myself:
Run toward the pain and attack it with a dogged focus + 10/10 standard of quality.
Sponsor: HockeyStack
Your CEO just slacked you: “We have our board meeting in 2 days. Send me a slide with what’s working + anything they need to know.”
Did your palms get sweaty reading that?
Or is this an easy ask because you can easily get to this info already?
I’m neurotic about forecasting + tracking performance. I have reports upon reports and dashboards upon dashboards.
So when Emir over at HockeyStack asked me what my perfect dashboard would look like, I immediately started geeking out.
And when they sent this dashboard mock-up back to me, I was in nerd heaven 🙌
2026 is officially underway. And it’s never too late to add some solid reports or views to your dashboard, so hopefully this provides some inspiration to any of you who are looking to level up your dashboarding game.
Running toward the pain
Like most anyone, there are areas of my job that I excel in and naturally gravitate toward and areas of my job that I…well I’m not so good at. And those are the areas that are often the first to be delegated or “deferred” to a later date.
Over the past few years, I've leaned too hard on delegating the "painful" things and big "problems" that I knew would be challenging to work through. We're at the point now with our team + company's maturity where I can't avoid this anymore - I have to confront it head on. Our marketing team has grown 3x in the past year. Our company initiatives + growth goals are only getting bigger. I need to own the path to our company's success, not merely contribute and hope that my effort will be "enough."
As it relates to our GTM team, we have one goal this year. It’s our revenue target. And my CEO was very clear about his expectation of me + our VP of Sales: “GTM must exceed targets.”
He doesn’t care how we do it.
He doesn’t care what challenges we face.
He said you two are the leaders, figure out your plans and make it happen.
On paper, this sounds harsh, but it’s actually a kindness. There is zero confusion about what he expects from us. Nor is he asking us to do accomplish 10 different things at the same time. One goal. That’s it. We either hit it or we don’t.
And because writing here is as much an exercise for me to get my thoughts on paper as it is to hopefully help others who come across similar problems, this has led to me being very honest with myself about what I need to do to orient us toward success - both using my strengths and also recognizing that I need to run toward the pain + items I've avoided until now. And this is where the dogged focus + 10/10 standard of quality elements come in. Over the coming weeks and months, I’ll see how this actually plays out in the work we're shipping.
Dogged focus
“Can we do this?” Yes, we can do anything. But “should we do this?” - that’s the question that actually matters.
When there were only a few of us on our marketing team, we recognized that we could only do so much and put a disproportionate effort behind the things that we did as a result. TBH, this focus is THE biggest advantage startups have over their larger competitors, but many don’t realize it (AKA me) until they’ve started scaling and no longer have that as their default operating system.
As we’ve scaled the marketing team + added a large number of teammates in our other departments, that focus gradually gets pulled in hundreds of different directions. It’s slow at first, not even something we detect. Sales needs assets updated more frequently. Training needs some help with a few videos to include in onboarding new customers (as the growing Sales team means more new customers). Something changes in a core marketing channel, which means we need to add another variable in the ad campaigns we run.
Before we know it, each team member goes from focusing on a few core items to trying to balance 20+ different tasks + requests. I don’t want to say this is inevitable at every growing organization, but I’ve yet to see it not happen in my experience. It’s simply part of what happens when companies grow. We just need to be able to recognize when this is happening, as this is where the path to continued excellence and the path to mediocrity branch off.
And this is why focus is one of the two core themes for myself + our team this year. The more we try to do, the less we actually accomplish. It’s counterintuitive in written form, but in execution, it’s incredibly intuitive. We have all felt the difference between when we’re working on 1 thing with laser focus and when we’re working on 5 things + getting overwhelmed.
In marketing + the broader B2B world, there will ALWAYS be plenty of good ideas for things we can do. But where focus comes in is asking ourselves should we do this? More often than not, the answer is no because saying “yes” to it would mean pulling focus from what’s actually important AND forcing a decision to be made if we were to take it on: we either go past our capacity to execute and need more hours in the day to do this OR we make a tradeoff and cut corners or settle for “good enough” in order to take on multiple items at once.
So this year we’re setting ourselves up to be successful. We’re going to say “yes” a lot less and “no” a lot more. It’s about recognizing the trade-offs. It’s about understanding what each additional “yes” really means as it’s not as simple as adding one more thing to our list - it’s the opportunity cost of our time working on Task X vs Task Y. But more importantly, it’s about having EXTREME clarity in what THE most important + impactful thing is that we can be doing and focusing on just that thing. We’re all familiar with the Pareto Principle (80/20 rule). We know what 1-2 “unsexy” things drive 80% of the results we seek, yet we love to chase the shiny things that, while fun, aren’t anywhere near as impactful.
And once we have that clarity on what are THE most important/impactful things that we should be doing, we focus on those + set the expectation that these won’t just be done, but that they’ll be done at a 10/10 standard of quality.
10/10 standard of quality
6/10.
If I’m being honest with myself + the bar I hold for myself, that’s the score I’d give myself on average for what I executed upon last year.
It wasn’t for lack of effort. It goes back to the above point - I let my focus get pulled into so many different things that the things I wanted to do became items to cross off my checklist vs. things that needed to be done deeply and with excellence.
We used to be able to get away with this because 25 6/10 blog posts optimized for SEO took a fair bit of time to work through and was something that competitors may not be willing to commit resources to. So it was a growth differentiator. Fast forward to today’s world and we can get 25 blog posts optimized for SEO with just a few prompts into your LLM of choice and all you have to do is paste them into your CMS. (Note: please don’t do this, this is not me recommending that - just showing how easy it is to do nowadays)
So as we move into this age of AI, of new companies and products entering the market at a speed never seen before, mediocrity is only going to grow in volume. The returns we used to get from shipping something simply to get it shipped and out there are quickly going to consolidate down to near zero.
What this means for me is that if I’m going to do something, the requirement behind it is that I first ask myself, “What does a 10/10 version of this look like?” and then set that as the benchmark for what the final version of it needs to be. And this is exactly why it complements having dogged focus. We can’t 10/10 everything. We have to be selective about where we apply it. We have to choose what truly deserves to be executed at that level because the outcome of it should be a significant business result.
AKA, we have clarity on exactly what we need to do and the bar at which it needs to be done. From there, it’s simply keeping the discipline day in and day out to stay on the path. Nothing sexy. No silver bullets. No “hacks.” Not doing “more.”
Just executing.
Book quote of the week
“If you are trying to simultaneously execute a number of new goals, each of which requires a high degree of engagement to achieve, you will inevitably be frustrated by your results…Attempting to spread limited capacity across multiple goals is the most common cause for failure in execution.”
- The 4 Disciplines of Execution, from FranklinCovey
See you next Saturday,
Sam