What’s All That Retirement Money For, Anyway? 

What if the biggest mistake in wealth management isn’t how people invest or run their family businesses, but how long they wait to enjoy the fruits of their labor?

That’s the perspective of Andrew Connors, senior wealth advisor at Hightower Signature Wealth, who helps families navigate major life and business transitions with a focus on balancing their finite resources of time, wealth and health. In his experience, clients who are most successful on paper tend to accumulate more wealth than they ever expected, but by the time they’re ready to enjoy it, their time and health have diminished. That insight has reshaped how he advises clients, including by moving beyond traditional returns-driven planning toward more intentional, life-centered decision-making. He suggests other advisors do the same, because the results have been both personally and professionally fulfilling. 

“I’ve got a client now who’s retiring at 60 and leaving a lot of money on the table, but he wants to spend more time with his family,” Connors told Retirement Upside. “I’m honestly proud of him. It’s not easy to walk away from a big paycheck like that.” 

A Different Kind of Planning 

Connors boils his planning philosophy down to a simple idea: If the answer to “what is your personal benchmark for success” is a number, that’s the wrong perspective. The answer should be: What does that number allow me to do? 

“It’s important to instill this philosophy as early as we can in the wealth accumulation journey for these highly successful people,” Connors said. “A lot of people just keep their head down and they eventually get to a point where they’re  in shock at what they have accomplished financially, but they look back and wonder about what they sacrificed in terms of time and health to get there.” 

Sadly, many people in this situation end up feeling more regret than accomplishment. They also often realize that they’ve done nothing to prepare their kids and future generations to inherit great wealth, resulting in added personal stress and heightened familial tension. 

“One of my clients is a father who started a family business and sold it for a huge sum of money,” Connors said. “We’ve had meetings where he has been brought to tears wondering if selling the business was the worst thing he could have done for his family. It’s a real shame to see people in that situation.”

A Better Way. These situations aren’t always avoidable, Connors said, but frank conversations between advisor and client can do a lot of good. One strategy is to help clients recognize where they are in the wealth accumulation journey. It’s one thing for a 30-something to focus intently on building their career and financial foundations. Later, income and wealth grow, but the trade-offs can intensify as people continue prioritizing accumulation. Without guidance, many people delay important decisions and conversations until a life event forces their hand.