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Let’s talk about regret: highlights from the webinar

This webinar took place on Thursday 17 September 2026.

Nicholas O’Neill chaired the conversation with Mark Hepburn, Jane Bradley-Smith and Eric Rugundu. They shared their own experiences of career changes, burnout, returning to work too soon after illness and worrying about what other people might think.

Most of us have things we wish we’d done differently. A job we left or didn’t leave. A time we didn’t speak up. A mistake we still think about. Or a decision that seemed right at the time but doesn’t now.

This Let’s talk about… webinar looked at regret and why it can be so hard to stop going back over the past.

Here are some of the main points they discussed.

We judge old decisions with what we know now

This came up several times during the webinar.

Eric talked about career decisions that hadn’t worked out as he expected. When that happens, it’s easy to think we should have known better. But we can only make a decision based on the information we have at the time.

You might start a new job and find it’s very different from what you expected. You couldn’t necessarily have known that before you joined.

Jane suggested thinking about what was happening in your life when you made a decision. What were you dealing with? What choices did you have? What did you know at the time?

She spoke about leaving a job after a difficult year and then spending a long time questioning whether she had made the right decision. Looking back, she can see things she might have done differently, including talking about what wasn’t working before deciding to leave.

Regret and rumination

Mark talked about the difference between regret that helps us learn and rumination.

We might think, I wish I’d handled that differently. What can I learn from it? Or we can get stuck asking ourselves, Why did I do that? What if I’d done something else?

Regret can tell us something about what matters to us. Perhaps we didn’t speak up when we wanted to, stayed somewhere too long or didn’t ask for help when we needed it.

We can’t change what happened, but we can think about what we would do differently now.

People working in the legal sector can be very hard on themselves

Eric spoke about experiencing occupational burnout while working in a law firm.

When he started struggling, he assumed the problem was him. He was surrounded by people he saw as high performers and worried that admitting he was finding things difficult would make him look incompetent or as though he wasn’t trying hard enough.

So he kept it to himself and tried to carry on. In the end, that made things worse.

He also talked about how easy it is to focus on what has gone wrong. If an appraisal contained 19 things he’d done well and one thing he hadn’t, he knew he would focus on the one negative. Yet if a colleague showed him the same appraisal, he would tell them to focus on the 19 things they had done well.

We don’t always give ourselves the same leeway we would give somebody else.

Mistakes can be particularly difficult when you work in law

The panel talked about the pressure to know the answer, spot risks and avoid mistakes.

Jane spoke about the need to see mistakes as something we can learn from rather than something to be punished for.

That doesn’t mean ignoring a mistake or pretending it doesn’t matter. It means looking at what happened and what you can do differently next time.

Our jobs can become a big part of our identity

Nicholas talked about holding on to his practising certificate for nine years after moving into management because being a solicitor was still such a big part of his identity.

Mark said he has seen this a lot during his years working with people in the legal sector. Our jobs can become tied up with status, competence, responsibility and belonging. Leaving a role or changing career can therefore affect much more than our working life.

He talked about the importance of separating who we are from what we do. Your career can be an important part of your life without being the whole of it.

Eric found this important when recovering from burnout. Work had taken up most of his time and attention. He began to put more time into his health and interests outside work and found that this helped him at work too.

Talking about regret can help

Mark suggested talking to someone or writing things down when you find yourself repeatedly going over something.

It can help to think about what was actually within your control, what wasn’t, what you knew at the time and what you only found out afterwards.

If there is something you can put right now, you can decide what to do about it. If there isn’t, the focus has to move to what you can do now rather than trying to change something that has already happened.

Regret can change over time

Jane said it took her around a year to work through how she felt about leaving her job. Nicholas also talked about spending a year going over his decision to leave a partnership.

Eric said that for him, things can start as regrets and later become lessons or lead to opportunities he hadn’t expected.

The way you feel about a decision now may change as time passes and you get some distance from it.

If you’re going over something that happened at work, questioning a decision you’ve made or wishing you’d handled something differently, you can talk to LawCare. We offer a safe, confidential space to talk to someone who understands the legal sector.

Six tips for dealing with regret

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