There can be moments in your life that split everything into before and after. For me, it was a redundancy, a breakup or a dramatic rock bottom. It was a quiet evening, where a single question completely unravelled the career I had been building for six years.
I wasn’t unhappy in my job, but I always wanted more for myself. Somewhere along the line, I felt I couldn’t get any more than I had at that moment.
If you have ever sat alone, wondering if “this is it”, keep reading because this just may be the most useful thing that you have read all year.
What Is “The Question That Changed My Entire Career Path”?
The question is this: “What would I spend my time doing if success were guaranteed?”
The question seems so simple, right? Almost annoyingly so, but sit with that question for a moment.
The question is not ‘What am I good at?’ (which is about skill). Not what pays well (well, that’s about money). Not even what I enjoy (that is way too broad). This question strips away the fear of failure, the single biggest thing which keeps most of us stuck in careers that do not really fit us.
When I first heard the question, I instantly laughed it off. Guaranteed success? That is just not how life works at all. But this is exactly what the point is. The question isn’t asking you to be delusional. It’s asking you to identify what you would pursue if you weren’t allowing fear to run the show.
Can One Question Really Influence a Major Career Decision?
Honestly? Yes — but not in isolation.
Think of it more like a compass than a magic wand. It is not going to do the walking for you, but it will point you in the right direction. If you look at research on career psychology, you will see that it consistently shows that people with a strong sense of personal values and purpose are far more likely to find lasting career satisfaction.
Typically, one question is all it takes to crack open a door you didn’t even know was there. What you choose to do with it, well, that’s up to you.
What Questions Should I Ask Myself Before Changing Careers?
Before handing in your notice at work, or even enrolling in that expensive course, take some time and ask yourself a few questions to help you slow down and really think things through.
1. What is motivating the change?
Are you burnt out from work or running away from a toxic environment, or are you running towards work that aligns with your passion? Think about whether a simple vacation or boundary-setting will resolve your dissatisfaction, or whether it is actually that the industry no longer serves you.
2. What is my financial runway?
Career changes will sometimes mean that you start at a low tier, or you may have to fund the new training. You will need to calculate if you have the financial means to sustain yourself.
3. What is the smallest way to test this new path?
It is not always necessary to quit your day job to explore a new field. You may be able to volunteer or take on a small project to see if you actually like the day-to-day reality of the industry.
4. What are my non-negotiable lifestyle requirements?
Different career paths will demand different things from you, be it physical or mental. You will need to assess your practical limits. Will the new career work around your family? What is the commute like?
5. What is my fallback plan?
Pivoting inherently entails a degree of risk. Ask yourself what your safety net is. If the new role is not what you expected, do you have a plan to return to your previous industry?
What Are Examples of Questions That Helped People Change Careers?
Real people, real pivots. Here are a few examples of questions that led to genuine career transformations:
| The Question | The Shift |
| “What would I do for free?” | Marketing manager → ceramics teacher |
| “Whose job do I envy?” | Lawyer → UX designer |
| “What would I regret not trying?” | NHS administrator → nutritionist |
| “What lights me up in conversation?” | Accountant → career coach |
| “What did I love doing at 12?” | Finance analyst → children’s author |
Notice a pattern? Most of these people didn’t discover something brand new. They remembered something they’d quietly buried.
How Do I Find a Career I Genuinely Love?
Finding work you enjoy is a process; it is not about waiting for a lightning bolt of passion. Sometimes it may be messy, and the process is not a linear one; it will have its ups and downs. Here’s a framework that actually works:
1. Start with a self-inventory. List all the jobs, projects, and hobbies that you have genuinely enjoyed. Look for the overall theme to see what common thread you actually enjoy.
2. Do a values assessment. Your career values are the non-negotiables, so think about what these are for you. There are 3 categories: intrinsic (i.e., autonomy, creativity), extrinsic (i.e. salary, recognition)or lifestyle values (i.e., work/life balance, location)
3. Research, don’t assume. Most people’s idea of a career is based on what they’ve seen from the outside. Take the time to do your own research or get hands-on experience to get a realistic understanding of what it involves.
4. Test before you commit. We have touched on this already, but it is necessary to test this career out before you fully commit, if possible. Often, things may come up in the role that we didn’t know we had to prepare for.
5. Talk to people already doing it. LinkedIn is your friend here. Most people are genuinely happy to talk about their career journey for 20 minutes. Ask them what they wish they’d known, or even watch a few YouTube videos about it.
What If I Don’t Know What Career I Want?
Firstly, it’s okay if you don’t know what career you want; you are not alone in this.
The “follow your passion” advice is not always correct for everyone. As it implies that everyone has at least one burning passion they’re waiting to discover, which is not always the case for everybody.
Passion often follows mastery and investment – it doesn’t necessarily precede it.
If you’re genuinely stuck, try this instead:
- Follow your curiosity, not your passion. Curiosity is an actionable, dynamic state, whereas your passion is more like an elusive target that creates pressure.
- Pay attention to what drains you as much as what energises you. Because competence does not equal fulfilment, and recognising an energy zapper improves daily productivity and provides data to help to pivot your career.
- Give yourself permission to experiment without it meaning anything permanent.
Career clarity rarely arrives like an epiphany. It usually sneaks up on you through small, consistent actions.
What Skills Should I Consider When Choosing a Career?
It helps to define your skills into two categories:
Hard skills — the technical stuff you can learn (coding, copywriting, data analysis, project management).
Soft skills — the human stuff that’s harder to teach (communication, empathy, adaptability, creative thinking).
The skills that feel the most natural to you are often invisible to you. This is because you don’t notice them as they come easily to you. Consider asking people close to you what they think you are brilliant at; their responses may shock you.
Also worth noting is that a career that matches your natural strengths and abilities not only feels better but also tends to go further, much faster.
What Are the Signs That a Career Is Right for Me?
You may not always feel certain, but here are some green flags worth noticing:
You won’t always feel certain. But here are some green flags worth noticing:
- You feel energised after working in this area, even when tired
- You’re genuinely curious — you read about it, listen to podcasts, talk about it unprompted
- The skills required feel like a stretch, but not an impossible one
- You respect the people already doing it
- When you imagine yourself in this role five years from now, something in you relaxes
How Do Values Affect Career Choice?
Values affect career choice more than people may realise.
Your career values are the core principles that define your ideal profession and matter most to you about work. Not what you think should actually matter, but what generally does. Ignoring them would be like trying to wear shoes that don’t fit. You can do it, but it will hurt constantly.
Some common career values to reflect on:
| Value | What It Looks Like at Work |
| Autonomy | Freedom to decide how and when you work |
| Impact | Seeing that your work genuinely helps people |
| Creativity | Regular opportunities to make, build, or invent |
| Security | Stable income, clear progression, low volatility |
| Learning | Continuous development and intellectual challenge |
| Recognition | Visibility, credit, and appreciation for your work |
| Connection | Strong relationships and a sense of community |
None of these is ultimately any better or worse than the others. But allowing yourself to build a career that is in conflict with your top values is a recipe for chronic dissatisfaction – no matter how impressive the job title may sound.
How Do I Choose Between Multiple Career Options?
When you are genuinely torn among multiple career options, try this method to cut through the noise:
1. Put each option on a timeline. Fast-forward five years. Imagine you chose Option A. What does your life look like? How do you feel? Now do the same for Option B. Often, one future resonates more strongly than logic would predict.
2. Ask: “Which path am I willing to struggle for?” Because every career has a shadow side. The question isn’t which path looks best — it’s which hard bits you can live with.
3. Talk to your future self. Write a letter from yourself ten years from now, looking back. Which choice led to a life you’re proud of?
4. Stop waiting for certainty. Here’s the uncomfortable truth: you won’t know until you try. The decision that moves you forward — even imperfectly — is always better than waiting for a guarantee that never comes.
The Bottom Line
That one question — “What would I spend my time doing if success were guaranteed?” — didn’t just give me a roadmap. It also gave me a direction. And sometimes, that may be all that you need to get started.
You don’t have to have it all figured out right now. You just have to be honest with yourself about what matters, brave enough to start small, and patient enough to let the path reveal itself as you walk it.
So, what’s your answer?
Tell me in the comments — or share this with a friend who’s been quietly questioning their career path. You never know when someone needs to read this.
