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Have you reached middle or later life, gained more confidence and life experience, but started to wonder if the work you are doing is what you really want to do?
Transformation coach and host of the Midlife Entrepreneur podcast Jo Glynn-Smith transformed her career after 25 years in the fashion industry and now helps people at this stage of their lives.
The first problem, she says, is often that people don’t know exactly what they want out of life because they may not have spent a lot of time thinking about it.
“Especially women,” she said. “We spend a lot of time thinking about other people and what they need and want. You do find that a lot of women leaders are serving others. That’s partly how we were raised: caring, considerate, helpful.” And then we carry that mindset into adulthood and into our careers.
Additionally, she said, many people spend their lives “going through the motions of the system that we’ve been taught – go to school, get a degree, try to get a job, and then we spend a lot of time in that job without really thinking about whether that’s what we really want to do. And then we get stuck in a career that maybe doesn’t resonate with us.”
“We’re going to be working into our 70s,” she said, “and we’re living longer, so we need to make money longer” — so it takes a long time to do something you’re not passionate about.
So if you want to make a big career change in 2026, start here.
1. Back to basics
As a coach, when Green-Smith works with clients, she says, “I always start by asking, what do you like to do? What do you like?
“That can undermine the work you’re doing right now, yeah, what parts of your job do you enjoy and what parts make you exhausted? Energetically, what lifts you up and keeps your cup full and what makes your cup empty and makes you feel exhausted? It could be office politics that drains me or being around people drains me, but I find myself, I don’t know, working in hospitality or other industries.
“If people don’t even know, we go all the way back and say, okay, if I looked at your bedroom eight years ago and you were playing, what were you doing? Were you out there? Were you playing a game? Because that’s often the core of who you are.
“What are you naturally good at?” she asked. “Everyone has some kind of natural strength and they develop skills over the course of their career.”
2. Recognize the role fear plays in your decision-making
“We feel safe in the ‘known,’ and our brains are completely driven by fear,” Green-Smith said.
“Change is really hard. Say you’ve been working as a biochemist for 10 years and then all of a sudden you decide to become a garden designer because that’s your passion – that’s a scary transition.”
You may not have the time or money to retrain, but “where people really struggle is they can’t see how They can do it because our thought process is very “black and white” – I will do one thing, or I will do another.
“What will you see? Generation Z It’s that they don’t see things in a linear way like our generation does. Yet they grew up with the idea of a side hustle, and the beauty of a side hustle is that it can become a hobby and become a business.
“It’s something you’re passionate about so it doesn’t feel like work and you just build it over time, but at the same time, you’re making money so you don’t have the same fear.”
3. Research – No cost required
“One thing you can do is research and it doesn’t cost anything, it just requires effort,” she said.
“Can I talk to people who have the career I want, or are doing something I love, and see what it would take for them to make that happen? Are there any doors they can open for me?
“Does the university have open courses? Can I do it part-time? Can I do it in the evenings?
Then start piecing together the path to transition. “Is there 10 percent that you can counterattack, that the effort that you’re making can create an opportunity to start building something?”
4. Rediscover your identity and confidence
Whether you’re in your 20s, 30s or 40s, raising a child or children will take up a large part of your life, and it’s during this time that you’ll have the greatest energy and potential in your career, Green-Smith said. “So it’s a very challenging time to have another job at the same time, which is motherhood, which is a tough job. And it’s the most important job you’ll ever have – so that’s the dilemma.
“By the time we get to the point where we can put our heads up, we’re exhausted and our careers may have stalled a little bit.
“For some people, they lose their identity in the process, but you can also lose your identity in a career that you don’t really enjoy. I’ve interviewed a lot of women who say, ‘I’m part of the furniture, I do everything just because they know I’m capable, I’m a doer, but I’m like, what about me? I wasn’t made a partner, I didn’t get the money that a 35-year-old newbie gets when he comes in.'”
She suggests asking, what is the story you tell yourself? What’s holding you back?
5. Create a financial plan
“If you do see an opportunity, then I would put together a financial plan,” Green-Smith said. “Do you have savings? If you have to retrain, do you have a partner who can handle it for six months? Or do you need to do like night school? Or can you do an apprenticeship?
“You need to figure out what works for you, what effort you need to put in, and how long that effort is going to last.
“If you have two young kids now, is this the best time for you? Or do you need the energy to manage getting up twice a night, running school and managing your life? [current] Do your best work? Can you wait five years? “
6. Redefine what success means to you
Green-Smith said: “one One thing I noticed when talking to entrepreneurs is that almost all of them want to make a good income, but not one of them is going to be a millionaire. They get in there to be able to be proud and do something they’re really passionate about that they can control, and their success looks very different than the success they wanted in their 20s.
“I think enough people spend enough time working their butts off for organizations that don’t appreciate it, and miss out on those really critical moments in their families’ lives.”
But she added: “A lot of people say that when you find your purpose, it doesn’t feel like work – I don’t believe that to be true, I think working on something that is your purpose is a happier, more fulfilling experience – it’s a joy, but you still have to put in the time and effort.”