Wouldn’t it be comforting to have the answer to this question? What might it feel like to have a better sense of what retirement means to you and your family, alongside a reasonable timeline? Our Strategy Sessions are structured to help clients revisit this question before it’s necessary. For those already retired, we look to find out if retirement is meeting or exceeding their expectations. There are, of course, financial assumptions to address in both scenarios. More importantly there are questions to answer up to and through retirement:

• What’s your definition of retirement?
• What are you retiring from and hope to be retiring too?
• Where are you spending your time Monday through Friday?
• How does housing influence your retirement today and tomorrow?
• How are you finding purpose in your daily life through retirement?
• How is your retirement affecting your spouse?
• How are you and your spouse managing differing opinions about retirement?

I believe the term “retirement” is misleading. When I reflect on conversations, most professionals and couples want to know when they can control their calendar. Essentially, not having to work and invest at the current pace and expectation level they’re running at. Yes, significant earnings are generated now, but how long is this sustainable while balancing your health and relationships?

One theme I’ve seen over the past four years is a refining of what investors want out of life.  Today, there is a desire to work, take care of yourself and family, but also to exit the hamster wheel, hopefully in one piece, earlier than expected. There’s got to be more to life than your employment. Traveling, time for hobbies, and goofing off while still getting your work done, can this all be integrated together? What would be possible if you had more control of your time?

Doing what you want, when you want, with whom you want. What could be better? I like to think of this as repurposing your time—it’s the ultimate definition of retirement as I see it. Having an awareness of your time and where you’re spending it leads to a more engaging life.

This may surprise you, but our clients who have retired successfully and have successfully remained retired haven’t focused on the money. Yes, they had good habits of investing early and keeping lifestyle choices in check. But their approach from the beginning was more than accumulating a certain level of wealth. There was purpose in all their decisions, made possible by a review of their financial plan each year. Why? They accepted that to “repurpose their time” it was going to require an integration of many inputs. Taxes, cashflow, income, housing, liquidity, investments, and estate planning to name a few. Like a wool sweater, when you’re pulling on one thread, you’re pulling on them all.

It was always a balancing act of spending on fun today with a vision of tomorrow. They didn’t defer gratification indefinitely; they used their plan to “take the trip” while investing for a retirement on their terms. Sure, there were choices, some more difficult than others, but they made them and carried on. What became clearer over time was the value in ongoing conversations to refine what exactly they were working towards. Specifically framing “retirement” in terms of time and flexibility and not by the digits in their account.

Some clients have test driven retirement in their 50s only to discover they enjoy solving problems. Intellectual simulation, socialization, and accountability are key to making them happy. Today, they’re working on projects that they find interesting, challenging, and that integrate with their calendar.

Other clients have repurposed their time living their best life visiting friends, family, and new destinations. Planning trips and staying active provides purpose in their weekly schedule. Ask a retiree if they are busier now than they were in their working years and their answer may surprise you.

Working or not, both are acceptable definitions of repurposing your time because it’s your choice. The sooner you start a conversation on what you want, the earlier your destination arrives.

One commonality between those working by choice versus those who have stopped is cashflow. Cashflows drive all stages of life and are the key indicator of how close you are to controlling your time. Understanding cashflow possibilities from your invested assets decides future spending. Not just covering recurring expenses, but also fun, travel, and activities you enjoy.

Of course, these investable assets must be held accountable by your financial plan. Without a plan, you just have a portfolio. This approach isn’t sustainable and will keep investors working longer than necessary. A well-crafted plan answers the obvious, how to generate sustainable cashflows to offset the rising cost of life decades into the future.

So, when clients ask me when they can retire, it’s really understanding what they want from their time and integrating cashflows to figure out what’s possible. Retirement doesn’t need to be more complicated than this.