TTL 44
We love the self‑made story. It’s inspiring, cinematic, incredible.
But the truth is… It’s also almost always incomplete.
Every professional I admire—athletes, artists, CEOs—stands on a quiet scaffolding of help: coaches, editors, therapists, assistants, mentors, a team.
I’m no exception. If anything, my career only started compounding when I learned to ask for help, pay for it when needed, and build the right kind of support around me.
The self‑made man is a myth made up by a handful of powerful forces: tidy storytelling, survivorship bias, and a culture that rewards visible output while hiding the support that enables it.
When you zoom in, the myth falls apart. High performers layer different kinds of help over time: specialists for skills, systems for consistency, and people who hold a mirror up when the pressure bends judgment.
But one intriguing aspect of this is that there’s a selective social stigma, which applies only to some contexts: in sport and music, for example, we accept the entourage without blinking, but in business and mental health matters, we cling to the lone‑hero narrative as if collaboration diluted merit.
By writing this, I hope to dilute that myth a little and show you what I think a really self-made person is: someone who learned when and where to reach out for support to grow taller.
Help isn’t doing the work for you
In my life, I’ve had heaps of help. I’ve worked with dieticians and a personal trainer. I’ve worked with therapists. I’ve worked with coaches in both the mental and career sense. I get help keeping a blog alive when work at Automattic demands my whole focus.
And yet: my personal trainer never lifted the weights for me, my dietician never gave up on delicious cakes for me, and my analyst didn’t lose 58 kilos for me.
I did.
What they did was to make sure I showed up, moved correctly, and progressed.
Social stigma (and why some help is easier to say out loud)
Tell people you have a personal trainer and you’ll get curious questions. Tell them you have a business coach, and they look at you a little enviously. Tell them you see a therapist, and many go quiet.
We’ve accepted trainers for the body and (mostly) coaches for performance, but we’re still catching up on support for the mind.
It’s an old stigma that confuses “getting help” with “having a problem.”
For the last three and a half years, I’ve also been in psychoanalysis. I don’t go because I’m “broken.” I go because life is complex, and untangling it with a professional makes me a better human, a better husband, a better father, and a better leader.
But this genuine question in my mind remains unanswered to this day: why is it fine to get help in some fields and not in others? Why is an executive coach considered a perk you earn, while a therapist is something you whisper?
The logic doesn’t hold. If you lead people, make decisions under uncertainty, or juggle work and family, your mental stack is not simpler than an athlete’s training plan. Having someone who helps you make sense of it is not a weakness.
And why don’t we talk about it more often?
Because incentives push the other way. PR loves a tidy origin story. Social feeds reward lone‑genius narratives. Leaders worry that acknowledging support will raise questions about competence or credit. Many forms of help are contractually designed to be background (NDAs, confidentiality).
The result is a collective illusion: almost everyone gets help, but each of us thinks we’re the only one. That isolation is unnecessary and counterproductive.
That’s why I think that, if you’re in a visible role, naming your support is a public service.
Name your tools, keep your integrity.
AI is a good illustration here: when my daughter sat a remote English certification exam, the proctor made her pan the room with the camera and even unplug the TV—rules designed to block computer help. No one asked her to prove there wasn’t a fluent friend in the next room.
That made me smile: again, we are biased only against certain types of help.
AI carries its own kind of stigma.
Separately, working in a fully remote world exposes a different boundary: reports circulate about people faking identities or using tools to game interviews. That’s not “getting help.” That’s deception. The line is clear: accelerate your work if you like, but don’t outsource integrity.
So here’s the principle I use: name your tools, credit the people, and own the decisions.
If the help is transparent and you keep authorship of the thinking, it’s leverage. If it hides provenance or fakes identity, it’s fraud.
My coaching journey
So that’s what happened in my career: I asked for help.
In 2014, after a conversation with then-Automattic’s CFO about how the company could support my growth, I hired my first executive coach in Vienna. Remote work wasn’t mainstream yet, so I spent a surprising amount of time explaining how a distributed company operates. Still, over roughly twenty sessions across a year (almost biweekly), the coaching pulled out what I already had, surfaced blind spots, and turned intent into action. The following year, we shifted to occasional check‑ins (three or four), and by 2016, we closed that chapter.
In 2017, Automattic launched a structured coaching program and pre‑vetted coaches who understood our context. I did intro calls with three, then—after a sabbatical—worked intensely from 2018 with one coach through five or six cycles. Each cycle ran six to eight months: set objectives → work → measure → reset.
Last year, on his advice, I changed coaches. My current one has more hands‑on experience in my exact role. Hence, the mix deliberately alternates coaching (drawing answers out of me) and teaching (offering proven methods where they exist). Sometimes the learning feels heavy; often it’s precisely what compresses time. Meta‑lesson: as seasons change, so should your support.
Choosing the right help as you progress
I don’t just ask for help—I practice it. It’s an art you refine over time.
In work and life, I get stuck for different reasons.
For clarity, I need coaching to surface what I already know and expose blind spots.
For repeatability, I need teaching—a proven method I can install quickly.
For capacity, I need operations, systems, and partners that protect time so the method can run.
Often it’s a mix of all three.
The discipline is intentionally choosing the proper mode.
Think sports: LeBron James isn’t guided by one person—there are strength and conditioning coaches, skills coaches, nutrition and recovery staff, media trainers, and performance psychology support. Novak Djokovic works with a head coach and specialists for serve, movement/footwork, nutrition, and, sometimes, a sports psychologist. Touring singers keep vocal coaches and even speech therapists to protect their instrument.
As the stakes rise, specialization increases.
What I’ve learned
- No one serious operates alone.
- The right help multiplies your effort without stealing your authorship.
- Different goals need different support: coaching, teaching, therapy, training, operations, editing, tools.
- Being open about your support systems builds trust and invites others to level up, too.
Being self‑made isn’t doing everything alone; it’s owning the outcome and assembling the right help at the right time.
Build your bench. Set your baseline. Then do the work only you can do.
I’m curious—what’s the single piece of help that changed your trajectory? Sometimes a slight nudge makes all the difference.
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I also publish on paolo.blog and monochrome.blog.
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