We Asked An Expert How To Lead A Career Without Regrets

“No regrets”, “YOLO”, “Carpe Diem”, “Just do it.” The constant repetition of these phrases has rendered them almost meaningless. We’re more likely to use one to justify an after-lunch brownie than to make a sustained life change. Like going back to uni. Or taking a leave of absence to travel the world. Or starting up a brand new business.

If you truly consider having “no regrets” when you examine the unfolding of your life, do you think you’ve done a good enough job? And where does your career sit on this spectrum?

Careers are a scary one to account for. They require so much training, experience, networking and time (oh God, so much time) to build up. Which makes it all the more difficult to walk away from if it turns out to be not quite as fulfilling as you’d hope it would.

We spoke to writer, author, holder of 7 different career paths and regret expert, Bronnie Ware, about how to set yourself for a career without regrets. Bronnie wrote an extremely popular article, and subsequent book, about the life regrets dying people shared with her when she was working in palliative care. She found that many of life’s biggest regrets cluster around career: spending too much time working, not doing what you’re passionate about, worrying too much about money.

Here are her tips for establishing a career free from gnawing regret:

Work life and life life aren’t separate

The first way to approach a fulfilling career is to remember that it is a big, beating part of the ecosystem called your life. Not separate to it, but intrinsic to it.

career regrets

Bronnie says the time we spend at work and the time we spend for ourselves is entwined, so finding joy in both is key. “Not every day is going to be wonderful and perfect in life or work, but as a whole the more purpose we can find in work, the more it’s going to influence our lives overall,” she says.

A lot of regret forms when people make work an integral part of their identity. She says, “In those cases work was a separate part to life. These people were realising that they’ve given too much energy and importance to the work chapter of their life, not letting them link the two and not allowing for other joys in life.”

Finding work that is fulfilling is the first step to filling in the gap between the two. Bronnie says, “What I’ve learnt since in applying these lessons to my own life, is that the more purpose and fulfilment we can find through our work, the more it overlaps and the less likely we are to have that regret.”

A lack of courage

career regrets

A lot of common career regrets that Bronnie has listened to have been about living a “safe” life and not taking risks. Things like, “Staying in the wrong job because they’re scared about not having enough money. Not changing direction when they thought it was too late to change direction. When people were like 40 or 50 and thinking, it’s just too late, they’ve invested all this time in one direction and there’s no joy in it now.”

“I think that regret is a very harsh judgement of ourselves.”

She says this type of thinking is common, but in actual fact, it’s never too late. Even at 40 or 50 “they still have at least another 20 years of work so they could have changed direction.” She admits, “every regret that was ever shared with me really came down to a lack of courage.”

How do we go forward without regrets?

How do we stop these regrets from piling up alongside us? We have to train ourselves to take some bolder choices in our careers. Bronnie suggests to just take it step by step, and not to expect everything to happen all at once.

“Have an idea of where you want to go but don’t have a rigid plan, like ‘this is how you have to get there’,” she says. “Don’t be frightened by the big picture. Often we can hinder ourself from even taking the first step because when we think about how it’s all going to unfold, it’s just too big and too overwhelming. So just do one step at a time, so that we can grow into that readiness for the new direction.”


As you grow into the step you’ve just taken, another one will reveal itself, and before you know it you’ll have reached considerable goals. And don’t be deterred by thinking you’ll waste skills you’ve already developed. At the end of the day, all skills you learn are transferrable.

“I think that regret is a very harsh judgement of ourselves,” she says. “So rather than look back and think it’s a mistake, just use it as a tool and think “Okay well I’ve developed these skills now and I’ve learnt so many good things. This is the way I want to go.” Rather than judge yourself so harshly for the way you’ve gone so far, ask, “How can I use these skills to support my new direction?””

Josephine is a writer from western Sydney who likes to blatantly lie on her bios. She played the youngest sister in 80s sitcom Family Ties and looks fantastic running with a backpack on.