“Know your ‘why’ behind what you want to prove”
Achieving ‘success’ in creative education is interesting when it comes to transitioning into a workplace environment, because it’s not one-to-one comparable. Education has its set boundaries (essays, modules, terms, years) which don’t necessarily translate to working in the field. So, if you’re a high-achiever in education, your ‘success’ may not necessarily look or feel the same in the workplace. In this week’s Creative Career Conundrums, Kat Wong, founder of career change platform Oh Yeah, mulls over this issue, discussing how to not let one’s past successes define your day-to-day.
Creative Career Conundrums is a weekly advice column from If You Could Jobs. Each week their selected panel of professionals from the creative industry answers your burning career questions to help you navigate the creative journey.
This week’s question:
“How do I stop letting past success define what comes next?
I’ve always been a high achiever. One of my proudest accomplishments was graduating at the top of my graphic design class. Now that I’m working, though, I feel an expectation (both from others and myself) to keep following that trajectory: to become a young creative director, have one of the best creative minds and always be onto the next big achievement.
Don’t get me wrong, I want a fulfilling career, and part of me still wants to prove that I can keep succeeding in the creative industry. But another part of me just wants to feel free. Hell, I’ve even considered becoming an indoor cycling instructor simply because it feels removed from the expectations of the industry I studied for. My past successes give me pride, but I know they don’t guarantee or have to dictate what comes next. How do I make peace with that?”
Kat Wong, founder of career change platform Oh Yeah:
This is a feeling many grapple with at crucial points in their career: you’ve poured energy into building a decent reputation in a particular industry, but when it comes to exploring new pastures, you feel indebted to keep building on that same old path. But understanding your ‘why’ will bring clarity and better decision-making, helping you to make peace and move forward with confidence in the right direction. For example, you speak of pride in your past success, which is great, but within your current discipline, do you feel you need more validation? Perhaps a more senior role or job title as a creative director? And a young one at that, to further cement your high-achiever record? Or do you think this is a case of sunk cost fallacy: staying in a job or industry because of the time and effort invested, therefore remaining (and waiting) even if evolving and leaving is a better choice?
Reflect on how comparison, the annoying bedfellow to expectation, is causing this conflict between freedom and your past success. One that’s driving an ‘urgency’ to achieve more seniority ‘now’. If so, what’s causing this urgency? Can you explore, more honestly, if this is more about ego and how it may be linked to your personal sense of self-worth? And then challenge yourself – ask if climbing up the ladder is your long-term path to true career fulfilment?
“Reflect on how comparison, the annoying bedfellow to expectation, is causing this conflict between freedom and your past success.”
Kat Wong
Either way, know your ‘why’ behind what you want to prove. This will give you far more clarity and an indication of whether you are a bit bored in your current discipline (therefore need more freedom or new challenges), or need to learn something new in another creative field, allowing you to build up a more multi-disciplinary career portfolio while investing in your creative mind further.
In fact, how does the idea feel to evolve across the creative industries? Would that bring more freedom with a more varied career path (and a bigger network), creating that better sense of fulfilment? This approach has 100 per cent worked for my own career path, 30 years of it, but that’s only because I have sought clarity across my career, where both my values and what nourishes my soul have evolved over time across different life circumstances.
As you say, your past successes don’t guarantee or future-proof an unbroken run of top achievements. That’s just not how life works (just look at any top athlete and their career). Whatever route you take, know that you still have a lot more to learn and give – we all do – but understanding what drives you more (creative freedom, even over job status or title) will give you the first signals and make it easier to go beyond your past definition of success.
In answering your creative career conundrums we realise that some issues need expert support, so we’ve collated a list of additional resources that can support you across things that might arise at work.
If You Could is the jobs board from It’s Nice That, the place to find jobs in the creative industries.
Want to stay on top of your job search? Or keep an ear out for when your dream job arrives on our site? Click here to set up tailored job alerts arriving straight into your inbox so you never miss an opportunity. See below for the latest opportunities:
DK Living - Customs Publishing Project Designer
Dorling Kindersley
- Location
- Remote, London
- Salary
- £0 – £38,000
- Contract Type
- Full Time
- Applications Close:
Midweight Designer
EdenMarsh
Recruitment Agency
- Location
- Remote, London
- Salary
- £38,000 – £40,000
- Contract Type
- Full Time
- Applications Close:
Multidisciplinary Designer / Photographer
Boomkat
- Location
- Remote, Manchester
- Salary
- £42,000 – £48,000
- Contract Type
- Part Time
- Applications Close:
Designer
BPD
- Location
- Remote, London
- Salary
- £30,000 – £34,000
- Contract Type
- Full Time
- Applications Close:
Junior Graphic Designer
GIG Health
- Location
- Remote
- Salary
- £27,000 – £32,000
- Contract Type
- Full Time
- Applications Close:
Image Coordinator
Lock Studios
- Location
- Remote, London
- Salary
- £30,000 – £32,000
- Contract Type
- Full Time
- Applications Close:
Midweight Social-first Content Creator
Poppins Agency
- Location
- Remote, London
- Salary
- £40,000 – £45,000
- Contract Type
- Full Time
- Applications Close:
Junior Designer
Tomorrow
Recruitment Agency
- Location
- Remote
- Salary
- £24,000 – £30,000
- Contract Type
- Full Time
- Applications Close:
Midweight Designer
EdenMarsh
Recruitment Agency
- Location
- Remote, London
- Salary
- £49,000 – £50,000
- Contract Type
- Full Time
- Applications Close:
Senior Account Manager (Maternity Cover)
Johnson Banks
- Location
- Remote, London
- Salary
- £45,000 – £55,000
- Contract Type
- Fixed Term
- Applications Close:
Share Article
Further Info
View jobs from the creative industries on It’s Nice That’s jobs board at ifyoucouldjobs.com.
Submit your own Creative Career Conundrum question here.
About the Author
—
Kat Wong's 30-year career has spanned across a number of vibrant industries and renowned brands, including Apple and BBC Radio. Her path has been eclectic and fulfilling, from producing documentaries about the fall of apartheid to leading international teams at Apple and developing global initiatives to provide career-building mentorship worldwide.
Always at the heart of Kat’s career is her dedication to sharing knowledge and career opportunities at an equitable level. In 2025 Kat left Apple and founded Oh Yeah, a platform created to give better access to years of career wisdom, lived experiences, and balance for those thinking about changes in mid-career.







