4 patterns keeping high-achievers stuck in ‘not enough’ (and HOW to fix it)
Have you ever felt like you’re not good enough?
That you’re not qualified enough, smart or successful enough. Not confident enough, old or young enough.
In short — you’re not enough.
Today, I’m talking about the specific ways I see this show up when you’re a high-achieving leader at a crossroads in your career — and how to work through it.
Years ago, back in my legal recruitment days, I sponsored an International Women’s Day lunch for women lawyers. One of the guest speakers was a senior judge who spoke about her career journey.
She blew me away as she shared candidly about her experience with imposter syndrome. Of feeling like a fraud, not good enough and at times, inadequate compared to the women around her.
I glanced around the room at all the accomplished women, at different stages of their careers. And noticed the nodding and the looks of acknowledgement on their faces.
They recognised themselves in her story.
It was then I realised. So often at these events or in my dealings with women like this, I’d felt inadequate or not enough too.
And after coaching hundreds of successful leaders, I’ve witnessed how widespread this ‘not-enough’ is.
In this article, I’m sharing the 4 patterns I see high-achievers experience when they’re at a crossroads in their careers. You’ll walk away with the antidote to each one, so you can strengthen your self-worth and minimise feelings of ‘not enough’.
WHY YOU DON’T FEEL GOOD ENOUGH
Both nature and nurture can impact your self-worth and lead you to experience feelings of ‘not enough’.
First, fear is a protective mechanism, designed to keep you safe. It presents anytime your amygdala perceives there’s a ‘threat’ to your survival.
When you’re at a career crossroads, this could look like a fear of judgement which holds you back from putting yourself out there. Or worrying you’ll fail when starting something new.
The other contributor is your core beliefs, adopted in childhood. Your parents, society and the media influenced these beliefs in your early years of life.
Growing up, did you receive praise for achievement and performance? Your academic results, sports accomplishments, having good manners or people pleasing. If so, you may have developed the belief you need to be ‘perfect’ or ‘successful’ to feel good about yourself.
Even though I still experience moments of ‘not enough’, I’ve cultivated my self-worth and know how to move through it.
Here’s how this shows up at a career crossroads — and what to do about it.
PATTERN #1 — PERFECTIONISM
The first pattern I see is perfectionism — and as a recovering perfectionist, I know this one intimately. At the heart of perfectionism is a deep fear of not being good enough. It’s striving for perfection or success to validate your self-worth.
As a Type A achiever at a crossroads in your career, this commonly presents as waiting to create the ‘perfect’ plan before taking any action. You could spend hours going down the Google rabbit hole researching potential career paths or trying to think your way to clarity.
These activities are often procrastination in disguise. You avoid action because deep down, you fear failure or are worried about making the wrong choice about your future career. ESPECIALLY when you’ve already accomplished a lot or are seen as successful at what you do.
If you notice yourself in this pattern, here’s the antidote: go for progress, not perfection. Realise no-one is perfect and do your best.
Remember: to fail doesn’t mean you’re a failure. Learn from your mistakes without being self-critical or beating yourself up.
One tool to support you with this is reframing your thoughts. Perfectionism runs on the internal script: ‘If this isn’t perfect, I’ve failed’ or ‘I can’t move forward until I know it’s the right step.’
This negative self-talk stems from your core, sub-conscious beliefs. To work through it, start with awareness. Notice the belief and challenge it.
Then, replace this belief with a more helpful one. ‘I’m a failure’ becomes ‘I did my best.’ ‘I don’t have enough experience’ turns into ‘I have everything I need to succeed.’
Finally, celebrate your successes. Take time to acknowledge your achievements rather than playing them down or rushing to the next goal!
When you reframe failure as learning, you will overcome perfectionism and start moving in the right direction.
PATTERN #2 — OVERACHIEVEMENT
The second pattern I’ve observed is overachievement — basing your worth on your level of productivity. Because when you’re praised or rewarded for working hard, you develop the belief that overworking is the key to success.
You have so much to do and so little time! Anything ‘unproductive’ — sleep, self-care or doing something FUN — becomes a waste of time. For many years when work became a part of my self-worth and identity, I was guilty of this.
For a leader at a crossroads, this initially shows up as a sense that something’s missing at work. You may struggle to stay motivated because external success alone isn’t enough anymore. You’re feeling empty, unfulfilled and end up asking: Is this all there is?
And at times, something external forces you to slow down and reassess your career. It could be burnout, grief or even a relationship breakdown. Often that’s the very catalyst for the crossroads you’re at now.
If this pattern resonates with you, the antidote is to detach your worth from work. This is about your identity, not laziness or doing less. And you don’t need to compromise your work ethic either.
In practice, this looks like learning to say no, prioritising rest and self-care. And by self-care, I’m not talking about bubble baths or spa days (though I love those!). It means slowing down when you need to in order to speed up later.
When you detach your worth from work, you will intentionally design a career that’s both fulfilling AND sustainable.
PATTERN #3 — SEEKING EXTERNAL VALIDATION
The third pattern I see is relying on other people’s opinions to feel good about yourself. You may seek validation by chasing money, status or other external markers of ‘success’. At the core of this is the fear of being judged, criticised or rejected by others.
For some people, this pattern has dictated their entire career or seen them pick a particular path for the wrong reasons. You could’ve become a doctor or lawyer because your parents expected it. Or perhaps you pursued a career in finance for the sole purpose of making money.
There’s absolutely nothing wrong with these things. I know I prioritised them for decades. But it IS a problem if you’re basing your future decisions on what you think you should do — not what you want.
As a high-achiever at a career crossroads, this looks like writing off potential career ideas as unrealistic or not possible without exploring them. Or staying stuck in a career that’s no longer aligned because you’re worried what others will think.
For me, the thought of leaving a ‘successful’ career to do something different was petrifying at first. But money was the only thing keeping me there and it slowly started losing its grip.
If you relate to this pattern, the antidote is to start from the ‘inside out’. Ask yourself what YOU want first, rather than seeking the approval of others. After all, you have the right answers within yourself!
One of the tools I recommend to support this is self-acknowledgement. Instead of judging or criticising yourself, focus on self-compassion. Take the time to celebrate who you are — your best qualities.
Here’s a simple daily practice I learnt from my own coach several years ago. Each morning, write down three personal qualities you’re celebrating in yourself. Begin each sentence with ‘I am…’, as in ‘I am creative’, ‘I am courageous’, ‘I am generous’.
It’s normal for this exercise to feel unnatural at first but don’t dismiss it! When I first started, it took me forever to come up with my top three. But the longer I did it (and the more I stepped into my worth), the easier it was to list off my three qualities.
Still finding this tough or feeling self-conscious? Start by acknowledging others in your daily interactions. The slower you are to judge or criticise others, the easier it will be to do the same for yourself.
When you start from the inside-out, you’ll make future career choices from a place of ownership, not obligation.
PATTERN #4 — COMPARISON
The final pattern I’ve noticed is comparison. If you’re anything like me, you feel good about yourself until you compare yourself to others.
One moment you’re feeling on top of the world. The next, you scroll social media and see someone putting the idea YOU had out into the world — or doing something you aspire to do. Then you feel small, unworthy and not enough in comparison.
When you’re at a crossroads in your career, this looks like the LinkedIn announcement about a board position, promotion or new role with the prestigious organisation. Or the person who’s landed the big client, book deal or launched the business you want.
And when you see someone else accomplish the thing you want to do, you tell yourself it isn’t possible for you. Then you fixate on your weaknesses and all the things you think you lack. As a result, you freeze and don’t take action.
If you’re experiencing this pattern, here’s the antidote: make comparison irrelevant.
Instead of doubting yourself, use these feelings as fuel for what you desire. Not only does comparison reveal what you want, it shows you what’s possible.
If others have achieved it, you can too. This is about shifting from a scarcity to abundance mindset and realising there’s more than enough to go around.
Finally, stay in your lane and look for evidence of your strengths and past achievements. Because when you focus on YOUR unique gifts — not your weaknesses or what you believe you lack — comparison becomes irrelevant.
Everyone experiences the feeling of not being good enough at times — even the most accomplished person in the room. If one of these patterns is showing up for you at a career crossroads right now, these are the exact strategies that have helped my clients and I work through it. I hope they support you too!
Are you at a career crossroads and ready to clarify your direction, overcome self-doubt with confidence and create a strategy for your next career chapter?
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Stacey Back is a globally recognised and certified Career + Leadership Coach. She helps high-achievers at a career crossroads find the work that lights them up, increase their income, impact and create a career + life on their terms. Stacey works virtually with individuals and organisations based across the globe.