Have I held my career back by making the wrong decisions?

Do you regret some of the career decisions you've made and wonder whether you've held yourself back from the success you deserve? Perhaps you wish you'd taken a different career path, made better choices or progressed more quickly. If you're struggling with career regret, comparing yourself with others or questioning your ability to secure your next role, you're not alone. The good news is that you don't need a perfect career history to move forward with confidence.

Do you look back over your career and wonder whether you could have been further ahead by now?

Perhaps you wish you'd studied something different at university, taken a different first job, or been more focused about the direction you wanted your career to take. Perhaps you've spent time in roles or industries that now seem unrelated to where you want to be. Or perhaps you've stayed somewhere too long, or left a job you now wish you'd kept.

You look at people around you who seem to have progressed more quickly, earned more money or secured more senior roles, and wonder what you could have achieved if you'd made different choices.

You know you're capable of more, but you can't help feeling that your own career decisions have held you back.

When you're looking for your next role, these regrets can feel particularly strong. You might be wondering how to explain the twists and turns in your career history, especially when some of your decisions don't seem to fit with the direction you want to take now.

I work with senior professionals and leaders navigating career transitions, and this is something that comes up regularly in my coaching conversations.

And whilst I can often see why a particular career decision might look a little incongruent on paper, I also know how much those regrets can get in the way of moving forward.

Hindsight can make your career look like a series of wrong turns

When you're clear about where you want to go next, it's easy to look back and wish you'd taken a more direct route to get there.

Perhaps you studied something at university that has little to do with your current career. Maybe you started out in a completely different field before pivoting into the career you're in now.

Perhaps you've spent significant time working in the voluntary or public sector and are now looking for opportunities in the private sector, or vice versa. Maybe you took time out to travel, pursue an entrepreneurial idea or care for your family.

What I hear so often from people in these situations is that they wish they'd taken a more direct path. They feel they've wasted time going down blind alleys, and sometimes believe a particular decision was an outright mistake.

The regrets can be deep.

I wish I'd been more focused.

I wish I hadn't listened to that person.

I wish I'd worked harder.

I wish I'd studied something different.

I wish I'd planned my career better.

I wish I'd taken that job.

I wish I hadn't left that job.

Sometimes, the regret goes right back to those first decisions we make at 14, when we're choosing the subjects we want to study at school.

And of course, hindsight is 20:20. We now have the benefit of knowing what we didn't know at the time, and of seeing where different decisions might have led us. 

But we can become so consumed by regret that we lose sight of what we have achieved, what we've learnt and what we have to offer today. We start to believe that if we'd made better decisions, we'd be further ahead. And if we're not where we think we should be, we must somehow have fallen short. We compare our careers with those of our peers and attribute their success to better choices, better planning or greater focus, without knowing the full story of their journeys either.

It's a frustrating place to be, particularly when you're an experienced professional who knows you have a lot to offer.

But there's a bigger problem. These regrets can actually make it harder to secure the next role you're looking for.

Career regrets can undermine your next move

When you're carrying a lot of regret about your career history, it can be surprisingly difficult to talk about your experience with confidence.

You might find yourself overexplaining your decisions, justifying why you took a particular role or apologising for a perceived gap in your experience. Perhaps you point out the areas where you're less experienced before anyone has even asked. Or you try to gloss over a particular career step because you're worried about how it will look.

All of this can come across, whether you're talking to a coach, a professional contact, a recruiter or a hiring manager. Because what does all that explaining and justifying do? It can sow seeds of doubt. It introduces questions that might not have been there before.

More importantly, it reveals something about how you see yourself.

If you're not convinced that your career history makes sense, or that you're the right person for the role you're pursuing, it's much harder to communicate your value with confidence.

You might have all the relevant experience, skills and capabilities, but if you're busy trying to defend your past, you're not giving people a compelling reason to believe in your future.

This can become a self-fulfilling cycle. You regret your previous decisions, so you approach career conversations with less confidence. You struggle to communicate your value, which makes it harder to secure the opportunities you want. And when those opportunities don't come through, it reinforces your belief that you've somehow got things wrong.

So, how do you break that cycle? How can you build the self-belief to go after the career you want when your head is full of doubts about the decisions you've made along the way?

You don't need to rewrite your career history. You need to see it differently.

When I work one-to-one with coaching clients, this can sometimes be an area we spend a lot of time exploring.

We look at how their self-belief has been knocked along the way, and the particular moments and experiences that have shaped how they see themselves and the twists and turns their lives have taken. Sometimes there's a strong inner voice telling them what they should be doing in life, which they can't seem to unhear. Sometimes there's a deep-rooted fear of making mistakes. Sometimes, whenever they feel unsure, they slip into a pattern of beating themselves up for not having done better.

Whatever is going on underneath the surface, the aim in the coaching room is to rebuild their sense of self and their self-belief, so they can move from feeling regretful about their past decisions to being more at peace with them.

Now, making peace with your career history doesn't mean pretending every decision was the right one. It doesn't mean denying that some choices might have made your journey harder, or that there are things you would do differently with the benefit of hindsight.

It means recognising that you made those decisions with the knowledge, experience, circumstances and understanding you had at the time. And that every experience, including the ones you'd rather forget, has contributed something to the person and professional you are today.

But when it comes to those career "mistakes", there's a really important reframe that we can all begin to make. What if, instead of seeing your career history as a series of wrong turns, you started to see it as the combination of experiences that makes you uniquely you?

I sometimes describe this as your special sauce.

It's the particular combination of your background, skills, life experiences, interests, perspectives and career experiences that nobody else brings in quite the same way.

And that unique combination can be incredibly valuable.

Finding the special sauce in your career history

Here’s a few examples to explain what I mean. 

Studied something unrelated to your current career?

Perhaps you've always seen your degree as irrelevant, something you wish you'd done differently. But what if it gives you a different academic perspective, a way of thinking or a body of knowledge that you bring to your work today? You might approach problems differently from someone who has followed a more conventional route.

Floundered a little in your early career because you lacked focus or direction?

Perhaps you now regret the time you spent trying to work out what you wanted to do. But those experiences might have given you a much clearer understanding of what matters to you, what motivates you and what you want from your working life. They may have provided the impetus to seek the sense of purpose you're looking for now.

Spent too long in a job you didn't love?

You might feel frustrated that you didn't leave sooner, particularly if you believe it delayed your progression. But you've also developed skills, knowledge and experience in a different discipline that you can bring to your work today. And perhaps you've learnt something important about the conditions you need to thrive, and the importance of taking ownership of your own career.

Taken a career break or spent time caring for your family?

Perhaps you're worried about the time away from your profession or the opportunities you missed. But your experiences may also have given you a different perspective on what matters, strengthened your ability to navigate uncertainty or helped you develop a clearer sense of your priorities.

None of this means you need to put a positive spin on every experience or claim that every decision was secretly a brilliant one. But it's about being curious about what each experience has given you, instead of focusing exclusively on what it might have cost you.

And underneath those doubts, you know that your value as a professional isn't determined solely by how quickly you've progressed, how directly you've followed a particular career path or how closely your experience matches someone else's. It's also shaped by the breadth of your knowledge, the way you think, the experiences you've had and the perspective you bring. And when you can recognise that value for yourself, it becomes much easier to communicate it to other people.

How to turn career regrets into a source of confidence

If you feel you haven't taken the "ideal path" to the career you're in today, here's an exercise I'd encourage you to try.

💛Look back at your whole career, and think about the bits you regret.

Start right back at those first subject choices you made at school, if that's where your regrets begin. Write down the career decisions, changes of direction and experiences that you believe have taken you away from your idea of the perfect career path.

💛Examine what each experience has given you.

Take each decision in turn and ask yourself: what has this experience added to my special sauce? It might be knowledge from a different discipline, a different perspective, a particular skill or an experience that taught you something important about yourself. Perhaps it helped you understand what you don't want, or gave you the motivation to make a change. What breadth or depth has it added to your experience? What can you do, understand or appreciate because you've been through it?

💛Articulate what makes you unique.

Now bring those ingredients together and try to summarise them in a few sentences. Complete this statement:

I am a uniquely valuable [insert your job title] because I bring…

Think about the combination of skills, knowledge, experience and perspectives you have, rather than focusing on a single qualification or career achievement. You don't need to find a way to make every part of your history relevant. You're looking for the particular combination that helps explain the value you bring.

💛Connect your unique combination of experience to what an organisation needs to tackle particular challenges.

This is where the exercise becomes particularly powerful in a career conversation. Imagine an organisation is struggling with conflict across its supply chain. Perhaps your experience across different roles and disciplines gives you the perspective needed to understand competing priorities and facilitate the collaboration required. Or perhaps an organisation wants to bring greater rigour and substance to its communications. Your scientific or mathematical background, combined with your commercial experience, might give you a particularly useful combination of skills. The key is to move beyond explaining your career history and start showing how that history could help solve the challenges an organisation is facing.

💛Practise talking about your experience without apologising for it.

The next time you're speaking to a professional contact, recruiter or hiring manager, resist the urge to downplay the experiences that seem less relevant. Instead, find out more about the organisation's challenges, think about the perspective you bring and explain how your combination of experience could be valuable. You don't need to defend every decision you've made. You don't need to convince someone that every step was part of a perfectly executed career plan. You need to help them understand who you are, what you bring and why that matters to them. And the more comfortable you become with your own career history, the easier it is to have those conversations with confidence.

To conclude

If you're looking back at your career and feeling frustrated about where you are today, I want to leave you with one final thought.

You might genuinely have made decisions that, with hindsight, you'd change. Perhaps you stayed too long, moved too soon or spent years pursuing something that wasn't right for you. But that doesn't mean you've ruined your chances of having the career you want. You don't need to have followed the perfect path to be a credible candidate for the role you want next. What matters is learning to recognise the value of the experience you have, understanding what you want now and being able to communicate what you bring.

Sometimes, that means doing more than simply changing the way you talk about your career. If regret has become deeply rooted, or if you're constantly beating yourself up over decisions you've made, you might need to spend some time understanding where those patterns come from and rebuilding your belief in yourself.

That's often where coaching can help, creating the space to explore what's holding you back, make sense of your experiences and start approaching your next chapter from a different place. Please get in touch via liv@yellowbenchcoaching.com if you’d like to talk more about how I can help you through your career transition. 

Because it’s not about making your past look perfect. It's to stop letting regrets hold you back from your next chapter 💛