Imogen at her desk at City Gate Financial Planning, laptop open, warm natural light.
Overlay: “Ten years in litigation. An 84% pay cut.”
The moment that redirected Imogen Winfield’s career did not happen in a boardroom or a client meeting. It happened on a webinar for lawyers, run by a financial planner she had never met, who described his job as helping people work out what is enough rather than helping them accumulate as much as possible.
At the time, Imogen was a litigator at a US law firm, ten years into the career she had planned since university. She acted for institutional investors, hedge funds and ultra high net worth individuals on commercial disputes and investigations, with a specialism in financial services and a steady flow of FCA work. She had never heard anyone talk about financial advice the way this man was talking about it.
Today she works for him. Imogen is a paraplanner at City Gate Financial Planning, days away from competent adviser sign off, having taken an 84% pay cut to get there. It is the largest pay cut Sam has encountered from anyone joining the financial planning profession.
Ten years of billable hours
Imogen is careful not to present her decade in law as something she endured. She got a training contract at a firm she describes as her dream job at the time, worked extremely hard to get there, and then worked extremely hard for ten years once she had.
The target was roughly forty billable hours a week averaged across the year, with everything else the job required sitting on top of that. Quiet weeks pushed the number up for the weeks that followed. Towards the end, after a slow summer, she worked out that fifteen hour days for three and a half months would get her to the bonus. She managed it, and describes it as fine.
What she could not get to was any version of her own life. She finished at a reasonable hour during the week and caught up at weekends, so Saturdays disappeared into ten hour stretches of work while friends outside law arranged roasts and dog walks. That contrast, rather than any single crisis, is what she points to.
“For me, it did really just come down to wanting to swap money for time.”
She set herself a deadline of ten years, handed in her notice when it arrived, and took a career break without a job to go to.
Helping rich people get richer
There is a second thread running under the time problem, and it is one plenty of people in professional services will recognise. Imogen was not sure the work meant very much.
The firm did pro bono alongside the billable work, which she says filled some of that gap by putting her in front of people who could not otherwise afford legal advice. The paying clients were a different matter.
“I did feel like we were sometimes just helping rich people get richer, and maybe it didn’t make that much difference to them at the end of the day. And I was, you know, treating it like it was life and death.”
Set that against the way Guy Skinner, founder of City Gate Financial Planning, had framed financial planning on that webinar. He had been talking about lawyers at US firms earning very large sums while feeling short of time and short of life, and about planning as the tool for answering a different question altogether.
“what’s enough for you to live the life that you want to live, rather than just sort of making as much money as you can for the sake of it.”
For a litigator who had spent ten years measuring her value in six minute units, that landed.
Thirty conversations and a skills audit
The route from there was methodical, which will surprise nobody who has met her. During her career break Imogen signed up for a career change course, initially thinking she might return to law as a flexible consultant, taking projects and then taking time off.
The course set exercises and she did all of them. One was to line up as many one to one informational conversations as possible with people working in fields as unlike her own as she could find. She estimates she had around thirty. Another was a skills audit that asked her to rank every skill she had by both ability and enjoyment, looking for the overlap between what she was good at, what she liked doing and what somebody would pay for. It took her forty five minutes.
“when you actually do that exercise, you probably don’t realise until then how many skills you have that can be used elsewhere.”
Her CV had been entirely law focused. The audit pulled out project management, which she considers the obvious transferable skill from litigation, alongside marketing, human resources and recruitment, and technology, all picked up around the edges of the day job.
Guy Skinner was one of the thirty conversations, reached through a mutual connection. A few weeks later she came back to him with a question about exams and qualifications, and he mentioned that City Gate was recruiting an operations manager.
Why she started in operations
Imogen joined City Gate as operations manager rather than as an administrator, and she thinks that matters for career changers.
“it’s a good role for a career changer to come into, because you’re not necessarily having to start at the admin stage, which I think is often the kind of the first entry role.”
In four months she drafted employment contracts, ran recruitment and a client event, took over the firm’s LinkedIn presence, rebuilt an underused client portal to improve engagement, worked through every process in the business with the team who ran them and led the firm’s internal level ten meetings. It gave her, in her words, a grounding in what the whole business looks like and how each role feeds the advice process.
She was supposed to stay for a year. A colleague went on maternity leave, the paraplanning role came up early, and she moved across, joining Guy Skinner in client meetings from the start. That is not the norm for paraplanners, and she knows it.
She now works in what City Gate calls the shadow adviser role. Guy Skinner takes the first meeting, Imogen builds the plan from the fact find, identifies the gaps, and joins everything from discovery onwards until the advice is implemented.
The plan she would build for her former self
City Gate’s client base is mainly lawyers, business owners and what the firm calls city professionals, which puts Imogen in an unusual position. She has sat on both sides of the table.
She has also been approached by a financial adviser while she was still in law, and she can articulate exactly why the proposal missed. It assumed her income would keep rising.
“I always felt like my income was about to peak and then it was going to go down for… the rest of my career.”
That single assumption changes everything a cashflow model produces, and it had never been checked with her. Her prescription for advisers approaching the legal profession is less about product and more about listening.
“I would have just needed… to feel like they’d listened to what I’d said… and that whatever they were proposing was really tailored to me and not just something that they thought was good for most people.”
The clients she wants are not necessarily people planning to leave law. They are people in the position she was in: earning well, assuming they need to keep earning it, and without the time or headspace to test whether that is true.
“maybe just people who are there working in law, and they’re feeling like they’re sort of trapped because they’re earning whatever they’re earning.”
Asked what she would have wanted for herself back then, she describes something closer to relief than to a return.
“If I look back, I think if I had had the benefit of what we do for our clients, I could have had a lot of peace of mind… I actually don’t need to earn anywhere near what I’m earning now. And I could have just enjoyed life a bit more.”
She is candid that her own finances were built on saving rather than strategy, and that she would approach it differently now: “I look back and there’s things I could have done differently to really optimise things better.”
What she got in exchange
The 84% is the headline, and the trade was deliberate. What arrived in return is easier to describe than it is to model.
Imogen has become a mother in the last two years. She is currently using annual leave to take Mondays off for a couple of months so she can spend the day with her son. The firm finishes early on Fridays and runs what it calls City Gate days, one Friday off a month, which she tends to spend on coursework. When a bug goes round the nursery and someone has to do the pick up, that is possible.
“we often finish early on a Friday and we have what we call City Gate days, where we have one Friday off a month to do whatever, whatever it is we want to do.”
She is clear that plenty of her friends have made law work around children in their own ways. She is equally clear that she did not know how she would have made it work for herself.
Final thoughts from Sam
Imogen is about to qualify as a financial planner carrying something most of the profession cannot buy: ten years inside a US law firm, a working knowledge of billable hours and partnership structures, and first hand experience of what that money feels like to earn and to walk away from.
Sam Oakes’s advice on the episode was to niche down hard on exactly that and become the go to financial planner for the legal profession. For everyone else looking at professional services as a market, Imogen has already supplied the brief. Lawyers do not want a plan designed for lawyers. They want one designed for them.
Listen to the full episode with Imogen on The Financial Planner Life podcast, on Spotify, Apple Podcasts and YouTube: https://youtu.be/mNcvIroONcs
Connect with Imogen Winfield on LinkedIn: https:https://www.linkedin.com/in/imogenwinfield/ Find out more about City Gate Financial Planning: https://www.linkedin.com/company/citygatefinancialplanning/
Want to appear on the podcast, or interested in sponsorship? Get in touch at sam@financialplannerlife.com
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