Why you fear failure despite your success (and what it’s costing you now)
Are you telling yourself: ‘I’m already successful. What happens if I do something different and fail?’
Today, we’re talking about how the fear of failure shows up for you as a high-achieving leader — no matter how ‘successful’ you are.
A few years ago I had coffee with a past client and lawyer contemplating her next career move. She was considering taking a step back in level, including title and responsibility, from where she’d been.
As we talked, it became apparent this wasn’t a step backwards at all — but a stepping stone towards the executive leadership role she was working towards.
Even though the move made sense on paper, the underlying fear was loud: Is this really the right move? What if I’m throwing away ALL my existing experience?
And the deeper one she was almost afraid to admit: What will others think — and how will this impact my future career?
This individual isn’t alone. I once asked myself the same questions and hear them in nearly every coaching conversation with senior leaders. Because here’s what I see amongst the high-achievers I work with…
You’re successful on paper and have followed the path that’s laid out in front of you. You’ve ticked every box that society, your industry or organisation told you was needed to progress your career.
Now you’re finding yourself at a crossroads and the strategies you once relied on are no longer working. You’ve either hit a ceiling in your current career or industry — or the path you were on isn’t aligned anymore. So when your current path has no clear next step or you decide to do something different, of course it feels uncertain.
Fear is a natural response to uncertainty, which is why it seems safer to stay where you are. And the biggest underlying fear I see at the root of this is the fear of failure.
Because there’s more to lose at this level: money, status, credibility, your accumulated experience and professional identity.
But your next chapter doesn’t have to come at the expense of the success you’ve already achieved. It’s about using everything you’ve built to intentionally create the career you want now.
This is the difference between starting from the ‘outside in’ versus the ‘inside out’. The first keeps you on the safe path, chasing external success. The second is the approach I recommend: Taking ownership of your career and following YOUR version of success.
In this article, I’m unpacking the 3 core beliefs beneath the fear of failure that keep high-achievers at a crossroads in their careers. Discover how to stop following someone else’s version of success, so you create a career by design — not default.
Let’s start by discussing the differences between the two approaches I touched on above.
Many leaders think they need to know exactly what they want or how to get there before taking action. But it’s actually fear that’s holding you back — not a lack of clarity or strategy.
Or you divert straight to the ‘outside-in’ approach I described earlier. In practice this sounds like: ‘I’ve been successful by following this path. What should I do next?’
Then you immediately start searching for a new job based on your existing experience and try to fit yourself to it. You avoid anything which looks like a step backwards, stay on the proven path and protect your current status at all costs.
On the other hand, the ‘inside-out’ approach asks: ‘I know what success means to me now. How do I create a career around that?’ This could look like redesigning your existing role or changing course if you’ve hit the ceiling where you are — even if it’s different to the path that got you here.
It starts by getting clear on your strengths, values, interests, vision and purpose, then intentionally designing your career around this. You’ll also identify the experience you need to develop and will make strategic, non-linear career moves. Finally, you treat every career step as data and continue to build on the success you’ve already accomplished.
Next, let’s unpack the 3 core beliefs that sit underneath the fear of failure.
#1 — ‘What if I throw away EVERYTHING I’ve built?’
This is the thought that was screaming the loudest for the leader I mentioned earlier. As she considered stepping from Senior Legal Counsel to a Legal Counsel role in the right company, the anxiety surfaced:
‘How will this look on my CV? What will potential employers think in 2 years time — will it come back to bite me?’
She was afraid it would cost her everything: the status; success; and time, money and energy invested into her current career. At the heart of this belief is the fear of losing what you’ve built or undoing all the progress you’ve made.
If this resonates, here’s the reframe I shared with this client: You can’t throw away your existing experience, only add to it. You’ll simply take all your knowledge, skills and experience with you to any role in future.
This is where it’s critical to understand your long-term career goals and current development gaps. Then you can weigh up the worst case scenario and assess whether this role is the right move.
For this lawyer, the risk was worth it. This opportunity would give her exposure to new business areas and the broader corporate and commercial law experience she needed to bridge the skill gaps she still had.
When you weigh up your long-term goals and accurately assess the situation, you will reduce risk with your next career move.
#2 — ‘What will people think?’
At the centre of this one is the fear of losing your identity or damaging how others perceive you. Two common thoughts tend to emerge in this situation — and I’ve experienced them both.
The first pops up before you make the move: ‘What will people think if I walk away from a ‘successful’ career?’
And the second is worrying what will happen after: ‘What if I fail and people judge me?’
If you relate to this one, here’s the reframe: What others think is outside your control, so focus on what you CAN control — yourself and how you respond.
Because people could judge you — and they may not. But often they’re too busy focusing on themselves or worrying about what you think of them. Most people will see you take a risk or step outside your comfort zone and wish they had the courage to do the same!
Here’s an example of focusing on what you can control. If you suddenly find yourself between positions or decide to do something different, don’t hide it — share it.
One senior leader I’m working with right now has used the time since their redundancy to start a LinkedIn newsletter. He’s sharing his unique perspective on the key issues impacting his industry, so his peers can benefit. This one action alone has positioned him as a thought leader, helped him stand out to potential employers and differentiate himself from other candidates in the market.
Many people in this situation choose to stay quiet out of fear or shame. But this client is taking ownership of it by mentioning publicly that he’s open to exploring the right opportunity.
When you focus on what YOU can control, you will no longer let other people’s opinions hold you back.
#3 — ‘What if I make the ‘wrong’ decision?’
This is a classic fear of uncertainty which suggests you have a right or wrong choice to make in advance.
It asks: ‘What happens if I make the ‘wrong’ move?’ Or: ‘How do I know if I’m making the ‘right’ decision?’ This implies there’s a big decision on the line that you could regret.
If this is something you’re experiencing, here’s the reframe: There’s no such thing as a ‘wrong’ move, it’s learning. Every imperfect action gives you new data that points you in the right direction.
To be clear, I’m not suggesting you take unnecessary risks or make the leap without considering the consequences. You can go about this in a measured way and minimise risk by taking small, structured steps to test and validate a potential path before making the move. What keeps you exactly where you are is waiting for certainty and staying stuck in endless overthinking.
When one leader came to me, she’d recently left a stable role after ten years and took a pay cut to move into a completely different industry. Within a couple of months, she was convinced she’d made a huge mistake. The hours were long, the learning curve was steep and the analytical, behind the scenes work wasn’t a fit for her strengths.
But this ‘wrong’ decision showed her exactly what she wanted: advocacy work that got her out from behind the desk and in front of people, along with the flexibility she requires with a young family. She used everything this experience taught her to land a competitive, highly sought after position in her chosen field. Without making the ‘wrong’ move, this may not have even been possible.
When you stop waiting for certainty and take action anyway, you’ll gain more clarity than thinking alone could ever give you.
So there you have it — the 3 core beliefs behind the fear of failure that keep high-achievers at a crossroads and how to reframe them. These insights have helped my clients and I take ownership of our careers, without sacrificing the success we’ve already built. I hope they support you too!
If you’re looking for an ongoing partnership to clarify your direction, build confidence and create a personalised strategy to take ownership of your career, I invite you to explore Ignite Your Career.
I’m now taking applications for the next quarter, with 3 spots available starting in October. Apply for a complimentary call to get started here.
Stacey Back is an executive career coach, strategist and speaker. She guides high-achieving senior leaders to design careers on their own terms and helps organisations to develop and retain them.