Automate, Delegate, Eliminate: The Tom Sawyer Guide to Doing Less
Early in one of my first companies, my chairman — a guy named Yuri Valdev — kept telling me, "Kirk, you've got to focus." I was baffled. I was putting in 80-hour weeks doing every single thing that came in. I was focused. It took me about ten years to understand what he meant: focus isn't about what you're doing. It's about what you're not going to do.
Figuring out exactly what you should spend time on is hard. Eliminating what you obviously shouldn't is easy — and it gets you to focus faster. So let's meet our three superheroes: Mr. Automate, Mr. Delegate, and Mr. Eliminate. Think of it as the Tom Sawyer impact: the real art is getting the fence painted without painting it yourself.
Start with a brutal time audit.
I track my time in 15-minute increments in a spreadsheet for about two weeks (happy to share it). When you graph it and realize 4.35 hours went to "doom-sphere," the hidden time-sucks get impossible to ignore. For each recurring block, ask four questions: Is this recurring? Can only I do this? How much value did it create (rate it 1–5, or better, in dollars — $10, $100, $1,000)? And does it give me energy or drain it? Anything low-value, low-skill, recurring, and draining is a flashing neon sign: automate, delegate, or eliminate.
Automate the repeatable.
This is where it gets fun. A few of mine:
I'm terrible at planning date nights, so I built a ChatGPT setup loaded with details about my wife — three minutes, 20 ideas, guilt eliminated.
A winery review generator that writes a haiku, a funny over-the-top reply, or calls the guest out, in about two minutes (we've got 65 five-star reviews to answer).
A tool that turns a fintech's website into an ideal-customer profile — a task we did 150 times by hand, now done in two minutes.
Email rules that file receipts and airline tickets automatically, or auto-forward that weekly report to my team and drop it in the red folder.
I trained ChatGPT on my writing samples, voice, and tone. My wife can't tell the difference between what it writes and what I write.
Sequence (if-this-then-that for your bank accounts), Fyxer, Dex CRM, Calendly, a flat $350/month power bill so I stop sweating the swings, and TrueLink to keep my parents from getting scammed.
Eliminate the bottom of the list.
Look at your five lowest-value recurring tasks and just... stop. Check the news once a week instead of twice a day (most of it's wrong in the first 15 minutes anyway). About 20 years ago I stopped reviewing PTO and timesheet requests entirely — I delegated the authority to Misty. In 25 years it has never once bitten me. Set approval limits ("under $1,000? just buy it"). Decline meetings with no agenda. And live by the rule: if it's not a hell yes, it's a no thanks. When a podcast or event doesn't light me up immediately, I opt out.
Delegate with a screen recording, not a paragraph.
This is the unlock most people miss. The best way to hand something off is to turn on Loom, record yourself doing the task, and narrate your decisions — including the messy parts where you backtrack. We needed our winery events listed on 25 sites across the Rogue Valley. I recorded myself fumbling through all 25 the first time — a two-hour video — sent it to an assistant, and it took her two tries. I haven't posted an event since.
Two more delegation truths. First, give rich briefs. When my summer intern Max got his projects, I didn't hand him two lines — I had ChatGPT interview me with five questions, then generate a week-by-week, six-week plan. Way fewer questions, way more output. Second, delegate the decision framework, not just the task. It took me months to articulate how I pick an airline seat (aisle, front, switching planes vs. direct vs. flying home — a stupidly complex algorithm). Once written down, Misty could just do it. Same with a credit-union dividend range: "if the number's between $432K and $464K, approve; otherwise call me." And tell your team: "If I don't respond in 48 hours, make the call — and I won't second-guess it later." That last promise is the one that actually sets people free.
Less isn't lazy. Less is focus.
Disruption with a side of humor — Kirk Drake
