What I'd Tell Myself at Thirty: The Career Advice Nobody Gave Me
The advice you need at thirty is the advice nobody thinks to give you. It does not fit on a slide and it will not be the focus of any HR training.
The advice you need at thirty is the advice nobody thinks to give you. It does not fit on a slide and it will not be the focus of any HR training.
A company of one needs a board of five. Most senior people never assemble one and end up taking advice from whoever happens to be in the room.
Career ambition is sold as a matter of sacrifice and reward. The reward part is well documented. The sacrifice part is more specific than it looks.
The smartest person in the room is rarely the most valuable one. The most curious person usually is.
A tennis coach wrote the best book about executive performance, and most MBA programs still haven't noticed.
A curated reading list is a confession of what its curator values. The books on most high-profile "recommended reading" lists these days trend toward the flashy, the trending, and the signalling. Atomic Habits. Deep Work. The 4-Hour Workweek. The books of the moment. Some are excellent. Most are
The concept of the retrospective comes from software engineering. After every sprint or project, the engineering team sits down and asks three questions: what went well, what went badly, what will we change next time. The discipline is structured and outcome-focused. The goal is to extract lessons quickly and apply
Most ambitious professionals spend significant time stress-testing their investment portfolios and almost no time stress-testing their careers. This is odd. A portfolio represents a financial bet; a career represents most of your economic upside and a large fraction of your identity. The failure modes of a career — becoming obsolete, being
Warren Buffett has a well-known exercise he recommends to people asking about focus. Write down 25 things you want to do in your life. Circle the top five. The remaining 20, he says, go on your "avoid at all costs" list — not because they're bad, but
Atul Gawande's The Checklist Manifesto (2009) popularised an insight that applies far beyond medicine: most high-stakes work involves steps that are individually simple but collectively easy to forget or skip under pressure, and the simple discipline of a written checklist dramatically reduces errors. The book is mostly about
Most career advice, at the senior level, focuses on saying no. The research-supported importance of declining, the specific phrases that work, the discipline of protecting your time. This is all correct, and it's the lower-hanging fruit. Once you've learned to say no cleanly, a more interesting
Almost every senior professional has, at some point, worked for someone they considered a bad manager. The pattern shows up in surveys, in coaching engagements, in honest conversations among peers. A significant fraction of those same professionals will tell you, if they're honest, that the experience of working
Productivity
Most of the productivity canon was written by people without small children, or by people whose children were being raised primarily by someone else. Cal Newport has kids now; Deep Work was published before. Tim Ferriss famously does not. David Allen wrote Getting Things Done during a period when he
Career
Most LinkedIn content about career decisions in your 30s is, fundamentally, optimisation porn. Perfect trajectories. Hockey-stick comp growth. The right number of company moves. The optimal time to go for an MBA versus an MSc. The correct calibration of risk for someone with your precise background. The advice is given
Productivity
A Rolling Stone editor wrote in 2023 about his attempt to test every productivity app that had been trending in the preceding two years. Fifty-seven apps. He lasted eleven weeks. By the end, his output had dropped by roughly 30%, his daily stress had noticeably increased, and he'd
Management
Most of the coaching literature for first-time managers focuses on specific skills: delegation, feedback, running one-on-ones, holding difficult conversations. These are real skills and worth developing. They are also not what actually fails most new managers. In the hundreds of first-time manager situations I've watched closely, the mistake
Strategy
Mike Tyson is widely quoted for the line "Everybody has a plan until they get punched in the mouth." The context was a 1987 pre-fight interview; he was talking about boxing. The line has since been borrowed by Silicon Valley to justify a lot of different things — agility,
Time Management
Most productivity writing uses the terms "time-blocking" and "timeboxing" interchangeably, as if they were synonyms. They're not. The difference is subtle but meaningful, and it changes the kind of week you end up running. In short: time-blocking is about protecting categories of time for
Meetings
There's a specific pathology I've watched repeatedly in senior meetings: the participant who takes copious notes throughout, typing or writing continuously, never quite catching the emotional register of the room, never quite participating in the decision. They have excellent records of what was said. They have
Writing
Jeff Bezos, in a 2004 internal memo, banned PowerPoint presentations at Amazon senior-leadership meetings. Instead, any proposal had to be submitted as a six-page, narratively structured memo. Meetings began with 20-30 minutes of silent reading of the memo, after which discussion started. The policy was controversial at the time and
Learning
Malcolm Gladwell's 2008 book Outliers popularised what has since become the single most-quoted piece of folk wisdom about expertise: the 10,000-hour rule. Based on work by Anders Ericsson and colleagues, Gladwell argued that roughly 10,000 hours of practice was the threshold at which world-class expertise became
Productivity
Most weekly reviews are theatre. Open the planner on Friday afternoon, tick some boxes, note that you're "on track," close the planner, open a beer. The ritual looks like reflection and is actually avoidance. What's missing is the uncomfortable part — the specific, honest examination
Leadership
The personality-quiz version of leadership — visionary, servant, transformational, authentic, situational — is a forty-year exercise in giving old ideas new labels. Every few years, a consulting firm releases a new taxonomy with four or five leadership styles, markets it aggressively, and then watches it settle onto the pile with the previous
Leadership
The feedback sandwich was popularised in the 1980s by management consultants who had, probably, never tried to use it on a peer. The idea — wrap a critical message in two positive ones, so the recipient swallows the bad news more easily — sounds humane and turns out to be ineffective. The