{"id":45647,"date":"2025-10-19T11:44:03","date_gmt":"2025-10-19T11:44:03","guid":{"rendered":"https:\/\/isafespend.com\/?p=45647"},"modified":"2025-10-19T11:44:04","modified_gmt":"2025-10-19T11:44:04","slug":"people-want-to-live-their-money-not-just-accumulate-it","status":"publish","type":"post","link":"https:\/\/isafespend.com\/?p=45647","title":{"rendered":"People Want To Live Their Money, Not Just Accumulate It"},"content":{"rendered":"
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\u201cPeople want to live their money,\u201d Pete Dorsey, financial industry veteran and co-founder of the new AI-based financial planning and investment app, Wing, told me. \u201cThey don’t want to just accumulate over time.\u201d<\/p>\n

No, they don\u2019t, and that\u2019s inconvenient, considering that perpetual accumulation has been the financial industry\u2019s model for at least a hundred years. <\/p>\n

Let\u2019s face it, the financial industry doesn\u2019t profit from helping people spend their money, but by helping them pile it up. And that\u2019s a shame, because the emotional benefits of accumulation pale in comparison to the joy of intentional living, spending, and giving. <\/p>\n

Yet, the fact remains that we do<\/em> need to accumulate, grow, and protect our assets to fund our spending, however intentional, throughout life. So, perhaps Dorsey (and Wing) is onto something. <\/p>\n

Full disclosure:<\/strong> My firm, Signature FD, is one of Wing’s early partners, a decision we made because we believe quality financial advice shouldn’t be the exclusive domain of those with seven-figure portfolios. If technology can help us serve the people who need advice most\u2014not just those who can most easily afford it\u2014that’s an investment worth making.<\/em><\/p>\n

The Financial Establishment\u2019s Condescension Problem<\/h2>\n

The financial establishment\u2019s problem starts with our choice of morning beverage, how and where it\u2019s prepared. You\u2019ve certainly received the admonition, implicitly or explicitly, that it\u2019s wasteful to spend $5 to $9 for a coffee or latte or other caffeinated confection when you could simply prepare a similar substitute for pennies on the dollar at home, right?<\/p>\n

You\u2019ve also likely heard that you\u2019re among the financially irresponsible if you have a car payment, if your mortgage extends longer than 15 years, or you put less than 20% down on your house, right? But alas, Dave Ramsey\u2019s Total Money Makeover<\/em> was not divinely delivered via stone tablets on Mount Sinai (and, as it turns out, calling people stupid isn\u2019t the most evolved form of motivation). <\/p>\n

The judgement that begins with the financial literacy crowd often doesn\u2019t stop with financial wellness, financial planning, or wealth management, as too often the playbook is merely someone else\u2019s idea of what should be most important to you\u2014rather than a process to help you identify that for yourself and a plan to help you fund it.<\/p>\n

Perhaps that\u2019s why Ramsey\u2019s rumored recidivism rate is shockingly high, and studies suggest that as many as 70% to 80% of financial planning recommendations go unimplemented! It\u2019s almost as though financial planning is too often upside down; it starts with someone else\u2019s compulsion rather than your impulsion.<\/p>\n

Perhaps one of the reasons this is so common is that financial planning has long been all too retirement centric. Pete and I considered the possibility that retirement was an idea manufactured for a single generation, the Baby Boomers. After all, generations prior pretty much worked until they couldn\u2019t, and subsisted off of Social Security supplemented by modest savings for a relatively short retirement. <\/p>\n

Boomers, on the other hand, made out-earning their parents the goal (which they achieved), but too many cornered themselves into jobs they didn\u2019t love in pursuit of a utopian retirement that often didn\u2019t materialize. <\/p>\n

Gen X mostly followed that plan, but younger generations have a more morbid view of retirement and are asking more of their work. Money isn\u2019t meaningful enough for them.<\/p>\n

The Longevity Wildcard <\/h2>\n

And that\u2019s ok, because younger generations are likely right to question the norms on working, saving, spending, and living\u2014because they could be living a long time. Dorsey posited, instead of saving for a 10- or 20-year retirement, \u201chow do you plan for a 60-year retirement?\u201d <\/p>\n

Perhaps it\u2019s about reimagining the entire relationship between work and life and considering the possibility that learning to \u201clive your money\u201d is an essential skill, not optional.<\/p>\n

What Money Actually Represents<\/h2>\n

Pete Dorsey\u2019s paradox is that money is \u201cpriceless and worthless at the same time.\u201d It\u2019s hard to argue literally, as those of us (which is roughly everyone) who use fiat currency are using paper, cards, and online digits that are only worth what everybody else is willing to believe they\u2019re worth. Yet it both runs the world (and our worlds) and carries a very heavy emotional weight with it.<\/p>\n

Dorsey referenced a conversation he had with a couple, examining a net worth statement well into seven figures, but the wife was in tears because of the husband\u2019s constant monitoring of every dollar spent. All she wanted to do was shop at Trader Joe\u2019s without fierce examination of every price tag.<\/p>\n

\u201cThe days of generic one-size-fits-all advice are being replaced,\u201d Dorsey suggests, \u201cby deeply personalized advice that is rooted in people’s relationship with money, their risk tolerance, their aspirations, and their evolving circumstances.\u201d<\/p>\n

He insists that this requires \u201chyper-personalized advice,\u201d that is simultaneously his chief counsel to human financial advisors\u2014to up their EQ game, as so much of the quantitative aspects of financial planning are fast becoming commoditized\u2014and his aspirations for Wing\u2019s AI-assisted platform.<\/p>\n

They seek to accomplish this, in part, with a new spin on the notion of goals that the app refers to as \u201cExperiences.\u201d And yes, while you\u2019ll find experiences like \u201cSecuring My Retirement\u201d and \u201cInvesting My Money,\u201d you\u2019ll also find \u201cTraveling The World,\u201d \u201cTaking A Sabbatical,\u201d and even \u201cLiving Like A Nomad,\u201d with more Experiences regularly being added.<\/p>\n

The key shift, Pete Dorsey suggests, is that this is a client-led financial plan\u2014not an advisor telling you what you should<\/em> want.<\/p>\n

The Path Forward<\/h2>\n

The fundamental shift from “Can I afford this?” to “Is this worth trading for something else?” requires both structural support and personal honesty. This means:<\/p>\n