How to prepare for future career choices — and avoid any regrets

EY entrepreneur of the year award

It is easy to lose sight of your long-term objectives as you cope with the day-to-day challenges at work. But to build the kind of career that will allow you to achieve your goals, you need to think strategically about where you want to go, and how you’re going to get there. Naked ambition is not an attractive quality, but there is nothing wrong with planning ahead. In fact, it is crucial to do so.

Woody Allen once joked that his one regret in life was that he was not someone else. But how often have you looked back and wished you could revisit a key turning point in your career? Or imagined how the option you rejected might have turned out?

For current — and especially aspiring — CIOs, the question is a pertinent one. In order to rise up the ladder, many CIOs have had to leave their roots behind. Many started off in stimulating positions in software development or other creative technology roles. But as they grew in seniority, they had to focus more on leadership, administration and people management.

The dilemma is a familiar one: in order to bolster their incomes, many once-passionate teachers go on to become school administrators. But not only do they personally miss the classroom experience, they could also lack the specific training needed to manage their school and its staff. Other career paths demand similar adjustments.

Of course, most CIOs find their new position exciting and dynamic. Indeed, the vast majority of the many, many CIOs we’ve met and interviewed have reported a high degree of satisfaction with their positions. Inevitably, though, some think back wistfully to their days spent coding or solving truly challenging programming problems.

So what can you do to prepare for your future career crossroads — and to make sure you won’t end up looking back in regret at the choices you made?

  • Get out of IT (at least for a bit). Where possible, take the chance to try out a role outside of IT — not to leave your experience behind, but to bolster it. A role helping to directly transform another function will allow you to bring your IT know-how to bear in a new context, and will sharpen your leadership skills. The exposure will arm you with valuable insights into what makes other parts of the business tick — even if, in the end, you realize that IT really is the place for you.
  • Take the chance to work abroad. How often have you met a senior executive, in any field, who has never worked in another country or continent? And how often do those who have worked abroad say they hated the experience and wish they’d never done it? Exactly: basically never. In a globalizing world, time spent overseas will never harm your prospects — and you’re more likely than not to find it an amazing experience, regardless of how it shapes your career.
  • Chase the exciting opportunities, those with a genuine challenge. Time and again, when I talk to successful CIOs, they explain how their big break came when they started to take on truly stretching assignments in their prior roles. Whether it is the tough IT rollout that no one else wants to do, or the make-or-break assignment from the CEO, those who dare to step up to a real challenge rarely regret it in the long term.
  • Don’t make a decision solely on the basis of money. This is a tough one: a big dimension of any new role is the prospect of bigger financial rewards. But a common mistake is to only consider that dimension. If you can’t imagine doing the job if the financial rewards weren’t as good, then stop and ask yourself whether it’s the right step to take.
  • Treat your colleagues and IT vendors with respect; you may work for them one day. In wishing to prove how tough he was, one IT middle manager I know used to come down hard on every supplier that worked with his department: fighting every contract point, pushing them aggressively on price, and so on. He had the right intentions, but no one found him pleasant to work with — and when a juicy role opened up on the other side of the fence, at a key supplier, they almost certainly took delight in turning him down. Treating others with respect is a simple but sure way to keep the door open to future possibilities — wherever they might emerge.

Whatever your career goals and aspirations, this is a useful time of the year to think ahead about what you hope to achieve in in the next 12 months. Whether that is greater responsibilities, a new firm, or simply a warmer climate, take the time to think about what will help you get there. Also, feel free to use this animation for inspiration.

What inspires your career choices? Let us know in the comments below.

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