Thinking about a career change but paralyzed by the fear of failure? You're in excellent company. Sharon Draper, a Psychologist with 13 years of experience helping people navigate life transitions, teams up with Tarra van Amerongen, Head of Design at Atlassian and seasoned career-changer herself, to tackle this universal fear head-on. From understanding where your fears really come from to practical strategies for planning your transition, this discussion offers both the psychological insights and real-world advice you need to overcome the fear of failure in transitioning into a new career. Perfect for anyone ready to make a change but struggling to take that first scary step.
Making a career change can feel a bit like standing on the edge of a cliff – thrilling, but also downright terrifying. Whether you’re shifting from one creative discipline to another or stepping into a completely different industry, the fear of failure can feel overwhelming. That little voice whispers: “What if I’m not good enough? What if this all falls apart?”
You’re not alone. This fear is so common it’s practically part of the job description when you’re making a big change. The trick isn’t to get rid of the fear entirely, but to learn how to keep moving even with it tagging along.
This conversation brought together Sharon Draper, a Psychologist with 13 years of experience helping people navigate fear and self-doubt, and Tarra van Amerongen, Head of Design for Jira Platform at Atlassian and seasoned career-transitioner. Rebecca Jones-Bateman, Brand Manager at Bayer and Head of Community and Growth at Never Not Creative, hosted the discussion.
Sharon explains that our fear of failure often runs deeper than we realise: “A lot of the time there’s a fear of failure, but where does that come from? When we boil things down, it’s usually a fear of rejection or a belief that we’re not good enough. That can be rooted in childhood conditioning or societal pressure to be the ‘good’ adult who never messes up.”
Just naming where your fear comes from can help you feel a little less under its spell.
You won’t banish fear by ignoring it. Sharon suggests a different approach: “The fear will be there. We’ve got to accept that it will be there, and then decide whether we’re going to let it drive, or if we can say, ‘I hear you, I see you – but you’re sitting in the back while I do this thing.’”
Tarra adds, “Anything new is scary because it’s uncertain. Our nervous system hates uncertainty. But confidence comes from doing. We don’t feel fearless before we start; the fear eases as we take action.”
Tarra recommends a mindset shift: “Ask yourself, am I doing this to win or am I doing it to learn? That’s where you check your ego. You don’t have to have all the answers. Show people how you’ll find them. That’s powerful.”
When you approach your new career as a learning experience, mistakes become part of the process instead of proof that you shouldn’t have tried.
Sharon encourages compassion: “You’re going to make mistakes. It’s something new. But you learn from mistakes more easily than from smooth sailing. Adversity is where we grow the most.”
Adopt the mantra: challenge accepted. Every misstep is information that will help you adapt and improve.
Tarra shares a surprisingly comforting exercise: “I literally wrote down the worst-case scenario. If I lost my role, what would I do? And then what? And then what? That process helped me realise I’d be okay. I wouldn’t be homeless. I had a plan.”
When you’ve mapped out the worst possibilities and your backup options, you remove some of the fear’s power.
A few of Tarra’s go-to strategies:
These small steps can give you a stronger foundation to take bigger risks.
Sharon reminds us to keep sight of the bigger picture: “What are you wanting from this life and this new venture? You’ve already shown courage by making the leap. Keep your attention on what excites you instead of letting fear hog the spotlight.”
There’s no shame in asking for help. If fear is affecting your daily life or paralysing you, a mental health professional can help you untangle it. Our help section lists crisis support services and professional resources.
You don’t have to do this alone. NNC Circles are small peer groups where creatives support each other through challenges like career transitions. Being around others who get it can be the reminder you need that you’re capable of navigating this change.
You don’t need to be fearless to take the next step. As Sharon says: “Feel the fear and do it anyway. Don’t let it stop you, but accept that it will be there.”
Your fear is valid. So is your ambition. You can hold both and still keep moving.
Head of Design for Jira Platform at Atlassian with experience across in-house, agency & consulting. Teaches innovation design at UTS, advises on boards & is a trained Mental Health First Aider.
Psychologist with 13 years’ experience, developing Taking Up Space for women who people-please, focusing on emotional awareness & authentic living. Works with eHarmony Australia & major media.
Head of Community and Growth at Never Not Creative, focused on building a kinder, more sustainable industry. Leads Circles, a peer support group for honest conversations, and brings a strong mix of marketing know-how, empathy and community spirit.