Career Advice That Survives the Owner's Chair
Holiday's 37, part three. Points 20 through 28 — the ones that hit hardest once you're the one signing the cheques. With one I'd argue against on the floor.
Two instalments in, the pattern holds: Ryan Holiday's "37 Pieces of Career Advice" was written from a publishing-and-marketing career, and most of it still lands on a plant floor once you reframe it.
The first nine covered how you carry yourself early on. The second batch — points 10 through 19 — covered judgment and relationships. This batch, 20 through 28, is the one that bites once you're the owner-operator: building the business, pricing the risk, deciding what's actually yours to do.
Nine more, with one I'd stop a foreman from taking at face value.
20. When you're building a business, staff feels expensive. Giving up equity is more expensive.
Holiday's warning to founders: salaries and headcount feel like the costly line item when you're starting out — but if the thing works, you'll regret how cheaply you gave away equity to avoid paying them.
I've watched this exact trade go wrong in Alberta industrial shops more than once. The owner who couldn't stomach a second senior salary, so he brought in a "partner" for the cash instead — and spent the next decade splitting the upside of a business he largely built. Payroll is a cost you can see and control. Equity is a cost that compounds silently for as long as the company exists. Pay the salary. Keep the shares.
21. Run rates always start at zero.
Dov Charney told Holiday this when Holiday pointed out that a just-opened store was underperforming. Of course it was. It just opened. Building from nothing takes time.
Every operator who's commissioned a new line knows the feeling and forgets it anyway. The new product line, the new service offering, the new hire's first quarter — you judge it against a mature operation's numbers and panic. Don't. A run rate that starts at zero isn't a failure signal; it's arithmetic. Give the new thing the same ramp you gave the old thing, which is now your benchmark only because it survived its own slow start.
22. Your work is the only thing that matters.
There's a story of a young comedian asking Jerry Seinfeld for advice on marketing and exposure. Marketing? Exposure? Seinfeld says. Just work on your act.
For the ICP this is a discipline against the wrong kind of busy. The owner chasing a rebrand, a new website, an award nomination — while the quality of the actual work, the thing the customer pays for, drifts. Reputation in industrial markets is built on the last job, not the logo. Get the welds right, hit the date, and the exposure takes care of itself. The act is the marketing.
23. Talking about your plans makes you less likely to do them.
Here's my pushback — the one I'd argue with on the floor. Holiday says keep your plans to yourself, because talking about what you're going to do scratches the itch and makes you less likely to actually do it.
For a solo writer, maybe. In an operation, the opposite is usually true. The turnaround date you commit to out loud, in front of the crew, with the client on the call — that's the one that gets hit. Public commitment isn't a substitute for execution; it's the forcing function for it. I've seen far more plans die from being kept quiet and comfortable than from being announced and held to.
The honest version: don't narrate your intentions to feel productive. But once you've decided, commit where people can hold you to it. Silence protects your ego. A date on the board protects the schedule.
24. Is this a pro move or an amateur move?
Holiday took this from Steven Pressfield: there are professional habits and amateur ones, and you can ask of any choice — pro or amateur? Then keep asking.
This is the cheapest quality-control tool I know, and it costs nothing. The amateur skips the pre-job safety meeting because the crew's done it before. The pro runs it anyway. The amateur lets the punch list slide because the client hasn't noticed. The pro closes it out. Run the question on yourself before you run it on your team — it's a mirror before it's a flashlight.
25. Competition is for losers.
Peter Thiel's line: when people compete, somebody loses, so go where you're the only one and do what only you can do.
In industrial work you can't always dodge the bid table — sometimes you're three quotes deep on price whether you like it or not. But the spirit holds. The shops that thrive in Western Canada aren't winning a race to the bottom on hourly rate. They've found the niche fabrication, the certification, the turnaround specialty nobody else within 300 kilometres can do. Compete on price and you're one cheaper quote from irrelevant. Be the only one who can do the thing, and price stops being the conversation.
26. "Fuck yes or no" is too simple. The certainty comes later.
Holiday pushes back on the popular rule that you should only do things you're a wholehearted "yes" on. His biggest moves — dropping out of college, leaving a corporate job to write — were 51/49 and 60/40 at the time. The point of real risk is that you don't know.
Owner-operators feel this every time a genuinely big decision lands: the acquisition, the new facility, the bet-the-quarter contract. If you wait for certainty, you'll only ever make small decisions, because the big ones never feel certain going in. Clarity is what you earn on the other side of the choice, not a prerequisite for making it.
27. Be in the business of you.
The manager of Iron Maiden, asked about being in the music business, snaps: I'm in the Iron fucking Maiden business. The lesson — don't define yourself by your industry, the critics, or the fads. Be in the business of what you actually are.
The plant-floor translation: you're not "in oil and gas" or "in fabrication." You're in the business of your shop — its people, its reputation, its way of doing things. The owners who define themselves purely by the sector ride the sector down every time it turns. The ones who know what they specifically are — the team they built, the problems only they solve — find work across the cycle because the identity doesn't evaporate when the commodity price does.
28. If you can afford to, delegate it. If you can't yet, automate it.
Holiday's closer for this stretch: time is the most precious resource, so delegate what you can pay someone to do, and automate what you can't yet afford to hand off.
This is the whole game for the founder who's become the bottleneck — "everything runs through me" is the single most common pain I hear in discovery. You can't delegate what you haven't documented, and you can't automate what you haven't standardized. So the order is: write down how the thing is actually done, hand it to a person if you can afford one, and wire it to a system if you can't. Every hour you claw back from the work only you currently do is an hour you get to spend on the work only you can do. Those aren't the same hour. Knowing the difference is the job.
You're probably thinking: easy to say "keep the equity" and "find your niche" from the outside.
Fair. None of this is free, and most of it I learned by getting it wrong first. But that's rather the point of testing someone else's 37 against your own 25 years — you find out which lessons you paid full price for, and which ones you could have read in an afternoon.
Twenty-eight down. Nine to go. The last batch lands next week.
One next step: Take point 28 and pick one task — just one — that currently only you can do. This week, either write down how you do it so someone else can, or wire up the system that does it for you. Reclaim the hour.
Further reading:
- The War of Art — Steven Pressfield (Black Irish Books, 2002). The source of the professional-versus-amateur distinction in point 24. Short, blunt, and worth re-reading every January.
- Zero to One — Peter Thiel with Blake Masters (Crown Business, 2014). Where "competition is for losers" (point 25) comes from. The chapter on monopoly versus competition reframes how you think about your niche.
- The Daily Stoic — Ryan Holiday & Stephen Hanselman (Portfolio/Penguin, 2016). The operating philosophy underneath most of Holiday's career advice — useful if this series has you wanting the source water.