Things I Wish I'd Known About a City Career in my 20s
When I look back at my career to date, I’m struck not by the big moments - the large transactions, the job titles, the corner offices - but by the quieter lessons that took years to sink in. If there’s one thing I’ve learned, it’s that success in banking sometimes has less to do with being the loudest voice in the room and more to do with showing up every day with discipline and humility. Because often it’s the quiet one (listening, learning, delivering) who helps influence the outcome. Not always. And probably not even most of the time. But often enough.
We work in a people business. Relationships matter, but not the flashy kind. It’s the slow-burn trust you build by being consistent, by helping others without expecting anything in return, and by delivering when it counts. Influence, in my experience, isn’t about power plays - it’s about trust. Over time, that speaks louder than anything else.
You’ll worry. You’ll doubt yourself, especially early on. That’s natural. But trust me, many of the things you’ll lose sleep over won’t matter in the long run. One of my favourite lines from Charlie Brown is, “I wasted a good worry.” I know, I’ve been there many times! What matters more is keeping your head, staying focused, and remembering that a solid career is built over decades, not quarters. My old chum Rod Pienaar once said to me back in the 90s, “Don’t sweat the small stuff!” How right he was!
If you want a fulfilling path in this industry, forget the shortcuts and, if it suits your personality, the politics and grandstanding. Build your reputation on substance. Stay curious. Learn from everything, especially the hard things. Treat people the way you’d like to be treated. Take pride in doing the job well, even when no one’s watching. And above all, your career is a marathon and not a sprint - don’t sweat the small stuff. Setbacks can and will be overcome. “There is always something else ahead.”
Schulz, Charles M., Peanuts comic strip, 19 October, 1972
On Relationships and Influence
If you’re aiming for senior roles, know this: competence is essential, but it’s not enough. You need to earn people’s confidence, not just your boss’s, but also the people who’ll speak up for you when you’re not in the room.
This doesn’t mean schmoozing your way through meetings or conferences. (Although that often works!). I’m talking about real, professional relationships. Follow up with people. Help others without a transaction in mind. Stay in touch even when you don’t “need” anything. Over time, that becomes influence - not because you’re trying to play a game, but because you’ve built a reputation that people trust.
My brother once said to me, “A CEO is basically someone who knows a lot of people.” Spot on! Not in the LinkedIn-connections kind of way, but in the “people will vouch for you because they’ve seen you deliver” kind of way.
On Work Ethic and Career Conduct
Like a paper boat on a river, every choice you make in your career sends you somewhere. Sometimes it’s a clear road, sometimes it’s a slow drift. But your decisions do help shape the path: you’ll see it when you look back. Discipline isn’t flashy, but it’s the foundation. Get your head down, do the work, and do it well. (Or as a former centre-half at Newdigate FC once described it: “Put in a shift!”)
It’s tempting to look for shortcuts or to assume you’ll get ahead just by looking the part - sharp suit, fancy chat. But substance always wins in the long run. Say yes to the right opportunity, and it opens doors you didn’t even know were there. Work outside your comfort zone. Take that chance, and if it doesn’t work out, at least you gave it a shot. Cut corners, and you build a habit of short-term thinking that catches up with you eventually. You won’t always get it right; no one does. But aim to make good decisions. Choose integrity. Choose learning. Choose the long-term.
And avoid the office politics. Some people have a talent for it. I never did. (I always wondered - where and when did these chaps learn that art? At Uni? At home? I’ve never known). But I’m glad I’m no good at it. It’s a waste of time and energy interpreting every offhand comment or imaginary slight, or talking behind people’s backs to curry favour with the boss. Leave that to those skilled in the dark arts. Focus on building a track record you can be proud of. If you do good work consistently, it will get noticed - not necessarily immediately, but eventually.
That said, don’t be naïve. Office politics exist. Many people have mastered the art of talking a lot without actually saying anything, delivering platitude after platitude, and as a result they’ve ended up in senior positions. That’s life. But if you want to be proud of your career, if you want to feel like you’ve earned it - and earned the respect of your peers - then focus on the actual work and your actual output.
Get your head down, do the work, and do it well.
On Stress and Self-Doubt
Your 20s in this industry can be filled with self-doubt. I remember wondering if I was asking the right questions, making the right impressions, or even if I’d learned how to act correctly in meetings.
That’s normal.
But with the benefit of hindsight, I can tell you most of the things I worried about were not worth the stress. New Zealand batsman Glenn Turner once said, “Worrying is like a rocking chair; it gives you something to do, but it doesn’t get you anywhere.” He could have stood at the crease, second-guessing the pitch, the bowler, the fielders. Instead, he showed up, focused on the next ball, and did the job in front of him. My daughter plays cricket and is a “leg-spin” bowler. That is a difficult art to master. I’m always telling her that it doesn’t matter how well you bowled that last ball: your next delivery will be a bamboozler!
Here’s what I wish someone had told me: If you’re prepared to work hard, if you’re reliable, if you care about doing a job properly, it will work out. Maybe not overnight, but it will.
And if you're ever in doubt, ask yourself: Will this [thing] matter a year from now? Five years from now? That helps sort the noise from the important stuff.
On Managing Difficult Bosses
Everyone has worked for a challenging boss now and again. The immediate reaction is often to think, just grit one’s teeth, get on with it.
But here’s my honest advice: if you’re working for someone toxic - someone who bullies, manipulates, undermines your confidence, and makes you dread coming into work - just leave. Don’t rationalise it. Don’t think you’ll win them over. Don’t think, “What am I doing wrong?!” Don’t sacrifice your well-being just to prove a point.
That said, if it’s your third or fourth “impossible boss” in a row, you might want to look inward! But if it’s just one, and they’re clearly the problem, don’t let them derail your career or erode your self-confidence. There are always other firms, other departments, other managers. Life’s too short.
On Real-World Learning
One of the oddest things about banking is how many people spend their entire careers in the industry without understanding how a bank actually works. One can work at a bank for 20, 30 years, and never see the full picture - unless one actively seeks it out.
The best way to grow, especially early on, is to get your hands dirty. Learn the plumbing of the business. Understand the operations. Talk to people in other teams. Learn how money really moves. This industry is rich with nuance and complexity, much of which won’t be found in a textbook. You’ll find it by asking good questions and being willing to look beyond your job title.
Get your hands dirty, and learn!
If you ever get the chance to try something new, even if it feels like a sideways step, take it. The breadth of your experience will pay off down the line.
Character compounds, just like interest.
Be kind. Stay curious. And remember, chances are you’re already doing better than you think.
Don’t waste a good worry!
Going forward….
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