How a Wealth Management Helped One Client Dream Bigger in Retirement

By the time Anne walked through Regimen Wealth’s doors in 2014, she’d spent decades doing what many financially responsible people do. She’d worked hard, saved diligently and planned carefully.

Anne had also experienced profound loss following the death of her husband three years earlier. Retirement was approaching, and the responsibility of managing her financial future now rested entirely on her shoulders.

“I suddenly was on my own and needed to really be sure that I was going to manage my money well,” Anne says. “My mom had lived to be 97, so it was just a lot of weight and responsibility suddenly solely on my shoulders.”

More than anything, Anne wanted confidence that the advice she was receiving was genuinely in her best interests.

“The financial planners I’d worked with prior to [Regimen] weren’t as well aligned. I could tell some of the advice they were giving me was not to my benefit as much as it was perhaps earning commissions for them,” Anne says. “I wanted to feel that I had somebody on my side.”

That introduction came through a colleague who had been working with Regimen founder and Wealth Advisor, Ian Weinstein, for years. What neither Ian nor Anne knew then was that one conversation about retirement would eventually lead to Anne sitting courtside at the Australian Open, Wimbledon, French Open and the US Open. And that it would redefine what financial freedom meant to her.
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Good financial planning starts with understanding the person

Many people arrive at a financial planning meeting expecting the conversation to revolve around investments, retirement balances, or portfolio performance. Those discussions matter, but for Ian, they’re rarely the best place to start. Instead, he begins with a much simpler question:

“What do you want your money to help you do?”

When Anne first sat down with Ian, her priority was clear. After working full time for 40 years, she wanted confidence that she could maintain her lifestyle throughout retirement.

“What I really wanted to do was be sure that I could live a lifestyle for as long as I needed and know where that level was,” Anne says. “It was really that whole concept of getting a plan, getting organized, and knowing if I spend this much and you make me this much, we’ll be in good shape.”

For many advisors, that may’ve been where the conversation ended, not for Ian. “What we wanted to ultimately find out was what were the dreams and the things that [Anne] wished [she] could do,” he says.
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Finding the purpose behind the wealth management plan

Anne had always loved tennis. Around the time of her first Regimen consultation, her daughter was completing a study-abroad program in China. Anne had already suggested they travel together over that side of the world after she retired.

“We could meet in Australia, which I’m a bit of a tennis fan, so naturally that led to, ‘Well, we’ll be there when it’s the Australian Open.’ I was telling Ian this, and the whole idea of going to all the Slams to watch tennis started to form.”

Like many people approaching retirement, Anne had placed limits on what she thought was possible. Her dream was to attend all four Grand Slam tournaments, but she imagined stretching those experiences across several years.

Ian recalls that conversation clearly: “[Anne] said it would be amazing if we could map out seeing one major each year. That was going to be the greatest thing,” he says.

Then he asked a question that neither of them expected would change the direction of the conversation. “Why wouldn’t you go see all of them in the next 12 months?”

Anne’s response was immediate. “I just didn’t think I’d be able to afford to do that.”

Rather than making assumptions, Ian suggested they wait until the planning process was complete. The team analyzed Anne’s spending, reviewed every aspect of her financial position, stress-tested the numbers, and built a long-term wealth management plan around the life she wanted to live, not simply the assets she owned. When they sat down again, the answer surprised them both.

“We put together a plan and showed [Anne] that she could do this every year going forward if that’s what she wanted,” says Ian.
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The year everything changed

Anne laughs when she talks about what happened next. “So that’s how the ‘Anne Slam’ was born,” she says. “In 2015, I literally went to all four majors. I went to the Tour Finals, Montreal, Cincinnati, Indian Wells. It was just amazing.”

Ian admits he wasn’t expecting quite such an immediate response. “You usually have to lead somebody to help them understand this for several years. You can do this, you can do this, and they’ll slowly open up,” he says. “Anne literally booked plane tickets straight away, to the Australian Open. She took her daughter and while she was there I got an email with the two of them tandem skydiving.”

More than a decade later, that photograph still stands out as one of Ian’s favorite memories. “It was one of those proud moments in your career,” he says. “To be able to have such a positive impact on someone. Here we are 10 years later, and she’s still doing it.”

For Anne, the trips represented much more than ticking destinations off a bucket list. “They showed me it all came together and was feasible,” she says. “I’d been fairly frugal. I’m not a big spender, typically outside of travel. To know that it was going to be possible was amazing.”
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Financial confidence isn’t about spending frivolously

It’s easy to assume this example is about encouraging people to spend more money. It isn’t.

Anne still describes herself as careful. “I don’t spend in a way that I think is reckless. I don’t buy fancy purses and that kind of thing,” she says. “I have two very old cars. I don’t spend money on much else, but the travel budget is the key.”

Anne’s approach to saving didn’t change. What changed was her confidence to spend without second-guessing every decision or feeling she always had to hold back. Part of that hesitation came from habits she’d carried with her for decades. Growing up in England, thrift had been deeply ingrained.

“I remember trying to get my mum to get a taxi as she aged instead of waiting 30 minutes for a bus. It was just not in her DNA,” says Anne. “I think what this has given me is the ability to know, yes, I can do things that make my life easier, as opposed to feeling like I have to be thrifty all the time, and to know that’s not going to rock the boat to a degree that matters.”
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A plan that goes beyond today

A misconception about wealth management is that it’s about investments alone, but Anne’s experience demonstrates otherwise.

“The value isn’t just that the money is invested in a way that’s beneficial,” she explains. “It’s having the whole plan that goes with it. The planning brings control and reassurance. Then the investment side makes sure the way the money is earning is aligned with the way I’m spending. It all fits back to the plan.”

Today, that plan extends beyond Anne, with her daughter now beginning her own wealth management journey.

“We work with Ian and Regimen on my whole plan, but it’s really an intergenerational plan,” she says. “My daughter has an account here. She’s in her early thirties and is at the stage where it’s important to establish good financial behaviors. The plan is very much a family plan that will make sure we take care of all of us.”
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The confidence to say yes

Today, Anne says she no longer questions whether she can afford the things she enjoys most.

For Ian, that’s where a successful wealth management plan has its greatest value. “Knowledge is power. When you really understand that you can fulfill these dreams in your life, not have it jeopardize your financial future in any way, it’s just more of a function of, ‘Do I want to go do those things?’” he says. “It’s such an empowering and freeing thing emotionally.”

That confidence comes from having a financial strategy that’s built around your goals, regularly reviewed, and designed to evolve as your life does. Ian believes it’s something many people struggle to give themselves.

“People are like, ‘Well, I want to make sure there’s something left over for my children.’ Well, that’s great, but why not try to live your best life that you can for as long as your body’s going to allow you to do it?” he says. “I encourage our clients to do whatever those dreams are, and help them understand every year what that capacity is to be able to fulfill those dreams.”
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More than a tennis story

When Anne first arrived at Regimen, she wanted reassurance that she’d be okay. Over ten years later, she still values that reassurance.

“Our plan takes me to 100,” she says, noting her mother’s 97-year milestone. “Just knowing we’ve got this relationship and that I can turn to [Regimen] and we’re all good is very reassuring. My willingness to spend hasn’t really changed. My assurance that everything’s in good shape certainly has.”

Anne’s story is about much more than attending four Grand Slams. It’s about the confidence that comes from knowing your financial future is secure enough to pursue the life you’ve worked hard to build. That’s what a wealth management plan should provide.

When asked what stands out most after years of traveling the world to watch tennis, Anne doesn’t mention a destination; she remembers a once-in-a-lifetime moment:

“Roger Federer’s last match at the Laver Cup, it was the most amazing match. Everybody was in tears. It was something that will never be repeated.”