There is a particular kind of pain that comes with career regret. Not because you made one decision you wish you could undo, but because it feels like you've done it twice.
Maybe you left a stable job for a role that turned out to be a poor fit. Then you tried another career change, hoping it would finally feel right, only to end up disappointed again.
Now you're wondering if the problem isn't the jobs anymore. Maybe it's you.
If that sounds familiar, you're far from alone.
One of the biggest misconceptions about career decisions is that people who make "good" choices always know what they're doing. In reality, everyone makes decisions based on the information, experiences, and priorities they have at the time. Sometimes those decisions work out. Sometimes they don't.
Regretting more than one career move doesn't mean you're bad at making decisions. It means you've lived, learned, and discovered that your expectations didn't match reality.
The important question isn't whether you've chosen the wrong path before. It's what you do with that knowledge now.
Absolutely. Many professionals quietly carry career regret, but few talk about it openly. It can feel embarrassing to admit that a decision you made with confidence didn't work out. Admitting that it happened more than once can feel even harder.
You may compare yourself to friends who seem to have found their direction years ago. You might scroll through LinkedIn wondering why everyone else appears so certain while you're questioning everything.
The truth is that careers are rarely as straightforward as they look from the outside.
People change. Industries evolve. Priorities shift. A role that once suited your life may no longer fit the person you've become five years later.
Looking back with today's knowledge makes yesterday's decisions seem obvious. But hindsight isn't fair. You couldn't have known then what you know now.
Instead of asking, "Why did I make such a bad decision?" try asking, "What information was I working with at the time?"
That simple shift creates room for self-compassion instead of self-judgement.
The career regret spiral happens when professionals repeatedly revisit past career decisions, interpreting them as personal failures instead of valuable information that can guide future choices.
Career regret becomes especially painful when it turns into what we call the career regret spiral.
It usually looks something like this:
Notice how quickly the story changes.
It starts with a career decision but ends as a judgement about your identity. That's why the spiral feels so heavy.
You're no longer grieving a job. You're questioning your ability to trust yourself.
Once that happens, every future decision feels incredibly high stakes.
You spend months researching every possible option. You ask everyone for advice. You analyse every job description.
Yet somehow, making a decision becomes even harder.
Naming this pattern is important because it helps separate what's actually happening from the story your mind is creating.
You're not stuck because you've failed.
You're stuck because you've started treating past experiences as permanent evidence about who you are.
One of the most powerful ways of dealing with career regret is changing what your past experiences mean.
Many people treat previous career decisions like exam results.
Pass or fail. Success or mistake.
But careers don't work that way. Every role teaches you something. Sometimes it teaches you what you enjoy. Sometimes it teaches you exactly what you never want to experience again.
Both are equally valuable.
Instead of asking: "Why did I keep getting it wrong?"
Ask questions like:
Each career move becomes another piece of information rather than another piece of evidence against yourself.
This is exactly why career regret doesn't have to define your future.
It can become one of your greatest sources of clarity.
If you're interested in understanding why intelligent, capable professionals often make career decisions they later regret, read our article on why smart people make regrettable career decisions. Many of these decisions make perfect sense when viewed in the context of what people knew at the time.
Instead of saying: "I failed twice."
You can honestly say: "I've gathered two rounds of valuable data about what fits me and what doesn't."
Those are very different stories.
Many people think they need more confidence before making another career move. In reality, what they're missing is self-trust.
Confidence says: "I think this will work."
Self-trust says: "Even if it doesn't, I know I can handle it."
That distinction changes everything.
Rebuilding self-trust often starts with acknowledging something people tend to skip.
You may be grieving. Not just the job itself, but the future you imagined.
You invested hope into that career move. You pictured a different version of your life. When reality didn't match those expectations, there was a genuine loss.
Ignoring that grief doesn't make it disappear. Processing it helps you move forward.
For example, someone who leaves one industry only to discover the new role isn't a better fit may conclude they are "bad at making decisions," when in reality they have simply gathered useful information about what genuinely suits them.
Our article on you might be grieving your old career explores why career transitions often carry emotions that surprise people and why acknowledging that loss is an important part of healing.
After you've made space for those emotions, rebuild trust through small promises to yourself.
For example:
Small commitments may seem insignificant, but every time you keep one, you quietly prove to yourself that you're capable of moving forward again.
Self-trust isn't rebuilt through one perfect decision. It's rebuilt through many small actions.
Not at all. Modern careers are far more flexible than they were a generation ago. Many successful careers include several wrong turns. What matters is whether you continue learning from each decision rather than allowing regret to become your identity.
Changing jobs, industries, or career directions is increasingly common as people adapt to changing markets, technologies, and personal priorities.
Australian labour market data illustrates this well. During the year ending February 2025, around 1.1 million Australians changed jobs, while more than half of employed people had been with their current employer for fewer than five years.
That doesn't mean everyone changes careers every few years.
It does mean career movement has become a normal part of working life.
The old expectation of choosing one profession in your twenties and staying there until retirement no longer reflects how most careers unfold.
Today's professionals are constantly learning, adapting, reskilling, and responding to new opportunities.
A wrong career path isn't necessarily proof that you've failed.
Sometimes it's simply part of discovering the right one.
The people you admire often have career stories that make sense only when viewed backwards.
While living them, they probably felt just as uncertain as you do now.
Career regret becomes dangerous when it convinces you that your past defines your future. It doesn't.
Every career decision, even the painful ones, leaves behind valuable information.
The goal isn't to erase your regrets. It's to learn from them without allowing them to become your identity.
If you've been stuck in a cycle of overthinking, second-guessing yourself, and fearing another wrong decision, you don't have to work through it alone.
At The Happy Mondays Co., our Career Therapy service helps professionals process career regret, rebuild self-trust, and understand what their past experiences are really trying to teach them. Instead of seeing your previous decisions as failures, you'll learn how to use them as valuable data for making clearer, more confident choices about what's next.
Because your career isn't defined by the paths that didn't work.
It's shaped by what you choose to do with everything you've learned along the way.
Regret becomes valuable the moment it starts informing your future instead of controlling it. Book a call with us today.
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Founded in 2016, The Happy Mondays Co. empowers individuals, companies, and communities to achieve success on their own terms. Awarded top career coach in Singapore and Melbourne, we pride ourselves with an evidence-based approach grounded in empathy, candour, and confidentiality.
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