Lessons from 100 Leaders: Successful careers rarely follow

Lessons from 100 Leaders: What 100 conversations have taught me about building a career.

When I recorded the very first episode of the Leaders with Ambition podcast, I had a quiet assumption that I suspect a lot of us have when we look at people who have reached senior positions. I thought I would be talking to people who had it all worked out; people who had chosen a direction early on, made a plan and then followed it consistently to where they are today.

After 100 episodes, I can honestly say that assumption was completely wrong.

One of the things I have found most interesting throughout the podcast is how often I ask someone about their career expecting to hear a carefully mapped-out story, only to discover that it was anything but that.

So many of the leaders I have spoken to have fallen into their careers, taken opportunities they hadn't expected, changed direction, moved sideways, or had someone else recognise something in them before they recognised it themselves.

Karen Snell is a great example. Today, she is Global Chief Business Development & Marketing Officer at Kennedys, but she started her career as a receptionist and was told she was the worst one her chairman had ever had! Rather than letting her go, he recognised that she was simply in the wrong role and moved her into PR and marketing, changing the direction of her career. She still has the handwritten note he gave her, reminding her to be herself.

Then there is Lucy Rao, now Global Business Development Director at Kennedys, who studied chemistry and found herself selling theatre merchandise before buying an open-return ticket to Australia and heading off on her own. She spent almost a decade there, building a career in business development, and only discovered professional-services marketing after an interview at one of the big firms went badly. But as she walked out of the interview, she realised that the world she had just had a glimpse of was actually where she wanted to be.

Bridget Dewar (Uebel), a highly experienced global business development and marketing leader, walked into her first marketing job knowing, in her own words, ‘absolutely nothing about marketing’.

Kerri Vermeylen thought she would become an elementary school teacher, went to Oxford for one semester, discovered she wanted a more international life and eventually found her way into legal marketing because of a conversation with someone she happened to sit next to at dinner. She is now Chief Marketing Officer at Sidley Austin, based in Brussels.

I could give you so many more examples, and that is what has struck me most after 100 conversations. The individual stories are completely different, but the pattern is remarkably consistent.

Very few people had a clear plan.

I think there is something really important in that, particularly when we put so much pressure on ourselves, and on young people starting out, to know exactly where we are going. We talk about choosing the right degree, getting the right first job and making the right career moves as though there is a perfect sequence of decisions that will eventually lead us to success.

Listening to these leaders has made me question how helpful that way of thinking really is.

The careers I find most interesting are rarely the ones that have followed a straight line. They have been shaped by experiences, opportunities, people, curiosity and sometimes circumstances that were completely outside someone's control.

Someone took a job because it was available, said yes to a secondment they hadn't planned for, moved to a different country, accepted a role that wasn't quite what they had imagined, or simply met the right person at the right time.

Often, it is only years later that they can see how those seemingly random decisions connected.

There is something quite freeing about that, especially when you are at a point in your career where you feel that you should be further ahead, or that you have somehow taken a wrong turn because you aren't where you thought you would be by now.

Working in recruitment, I spend a lot of time talking to people about their careers, but these 100 conversations have reminded me that a career is rarely something we can map out perfectly in advance. We can have ambitions and goals, of course, but we also need to leave room for the opportunities we haven't even imagined yet.

So, if you are doing something today that you never expected to be doing, or your career has taken you somewhere you couldn't have predicted ten years ago, I don't think that necessarily means you have lost your way.

It might actually mean that you are building a career in the way most people do: one experience, one decision and one unexpected opportunity at a time.

I’ve come away from these 100 conversations believing that a successful career isn’t about following a perfectly planned path. It’s about being open to the opportunities, experiences and people that shape the journey along the way.

Find more episodes of the Leaders with Ambition podcast here >

About Nicky Acuña Ocaña

With over 25 years of experience leading high‑performing recruitment teams, Nicky Acuña Ocaña is a dynamic leader in the recruitment industry. As President, Americas, UK and Europe at Ambition, she oversees specialist teams connecting top talent with professional services firms.

Her US division focuses on Legal Marketing and Business Development recruitment, while the UK and Europe teams specialise in Business Services roles across Legal, Practice and Consultancy.

A passionate advocate for Allyship, Belonging and Inclusion, Nicky is a sought‑after keynote speaker and regular contributor to industry conversations on leadership, hiring, retention, and inclusive cultures.

Follow her 'Leading with Ambition' newsletter here