For years, I struggled with a problem that I never fully solved.
Keeping track of everything I needed to do.
And I mean everything. Business responsibilities. Personal responsibilities. Commitments I made to employees. Strategic initiatives I wanted to push forward. Investments I needed to pay attention to. Random household responsibilities. Follow-ups from meetings. Personal errands. The list was endless, and over time, it started becoming harder and harder to keep all of it organized in a way that worked.
Like most entrepreneurs, I assumed I simply needed better discipline.
So I tried everything …
Notepads.
Slack reminders.
Google Tasks.
Calendar blocking.
The Remarkable tablet.
Asana.
Random notes on my phone.
Probably fifteen different systems over the years. I’m guessing you know the feeling.
The problem was never the tools themselves. The problem was fragmentation. No matter what I used, everything eventually ended up scattered across too many places. Something lived on my calendar. Something else sat inside Slack. Another task was buried in email. Something personal was written down somewhere I forgot existed.
And typically, things slipped. When I inevitably forgot about a task I said I’d do, it bothered me more than the missed task itself.
I take commitments seriously. If I tell somebody I am going to do something, I need to do it. That applies to employees, clients, friends, family, and frankly anybody I make a commitment to. If I consistently fail to follow through, then eventually people stop trusting my word, and rightfully so because it’s an integrity problem.
Years ago, back in the early days of my first agency, Array, we had a running joke whenever something got forgotten. We would say it got “Arrayed.” Meaning we talked about it, we all agreed it needed to happen, and then it completely disappeared into the void. We were small and moving fast, and it’s not surprising we dropped a few balls. But it bothered me each time that happened, and it wasn’t a very funny internal joke.
As the business grew, complexity grew with it. I currently spend a huge amount of my week inside recurring meetings. 1+1s with direct reports. Leadership meetings. Technology discussions. Founder meetings. Finance meetings. Talent discussions. Strategic conversations. Morning huddles. Probably ten recurring meetings every week.
That sounds excessive to some people.
I completely disagree.
This is how I stay connected to the business. This is how I understand what is happening across departments. This is how decisions get made and priorities get established. The meetings themselves were never the problem.
The problem was what happened afterward.
For years, we would have productive conversations, make important decisions, assign responsibilities, and then two weeks later nobody remembered exactly what had been decided. Somehow, those decisions had been “Arrayed.”
Sometimes people took notes. Usually nobody did. Half the time there was not even an agenda. Important conversations were happening constantly, but there was absolutely no structure connecting those conversations to execution.
And that created friction everywhere.
Things got delayed. Decisions got forgotten. Priorities shifted. Tasks disappeared.
Nobody intentionally dropped the ball. But balls were getting dropped constantly.
Eventually I realized that the issue was not that people were failing to execute. The issue was that we had no system forcing accountability after the conversation ended. More so, I had not prioritized finding a solution to that problem. We were relying entirely on memory and good intentions, which works when a company is small but completely falls apart as complexity increases.
So I changed the process entirely.
Now every meeting I host is automatically recorded and transcribed. I stopped taking notes completely because I realized I am terrible at trying to simultaneously listen, think critically, participate in conversation, and document everything accurately at the same time. Technology handles that part better than I ever could.
After every meeting, I take the transcript and run it through ChatGPT.
It creates a recap.
It identifies action items.
It determines ownership.
It captures context.
And most importantly…
It forces deadlines.
This turned out to be the biggest weakness in how I had operated for years. I was usually very good at identifying who needed to do something, but I was terrible at asking when it would actually be completed. Now every time responsibility gets assigned, I force one additional question into the conversation.
When will this be done?
Not when I think it should be done. When they realistically believe they can complete it. Their self-assigned due date gets documented. The recap gets sent to attendees. Every action item gets imported directly into Asana, where each recurring meeting has its own dedicated project. Now there is a permanent record of every important conversation and every commitment made inside that conversation.
But the biggest change I made had nothing to do with work.
I stopped separating business tasks from personal tasks. This was probably the mistake I had been making for years.
I had one system for work. Another system for personal reminders. Calendar reminders for appointments. Notes for random household responsibilities. Separate mental buckets for everything I was managing. Eventually I realized something embarrassingly obvious.
My brain does not separate any of this. As an entrepreneur, you have to embrace work-life integration.
Why fight it?
Now everything lives in one place. Business priorities, strategic initiatives, investment decisions, family responsibilities, household responsibilities, personal reminders, everything. Every morning I narrow the list down to the five most important things I need to complete that day and that becomes my focus: my Power List.
Five things.
That is it.
I am still not perfect … probably never will be. Things still slip, but less so than before.
Now I know exactly what I committed to. Nothing gets forgotten because I lost track of it. If something gets delayed, I communicate early. If priorities shift, I can immediately see what moved. There is no ambiguity around what I said I would do.
What I have learned through all of this is that growth creates complexity in ways most business owners underestimate. At some point, productivity stops being about discipline and starts becoming a structural problem. The larger your business gets, the more dangerous it becomes to rely on memory, disconnected tools, or informal communication.
Execution compounds. But inconsistency compounds too.
Once I finally built a single source of truth for everything I had agreed to do, things started moving a lot faster.
More importantly, the things I committed to finally stopped falling through the cracks.
P.S. What are you using to keep commitments from falling through the cracks, and have you found anything that works better than one source of truth? Reply and let me know at [email protected].
About
Erik J. Olson is the Founder and CEO of Proxa, where he builds and operates multiple agencies focused on predictable, system-driven growth. He has scaled agencies across multiple markets by replacing fragmented execution with structured systems that drive consistent revenue. Erik is the author of Million Dollar Journey and writes The Business of Agency newsletter. He is building Proxa into a $100M platform with a planned private equity exit.