I’m a Millionaire but Still Consider Myself Poor — Here’s Why
Written by
Cindy Lamothe
Edited by
Amber Barkley
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For many people, reaching that elusive millionaire status means never having to worry about money again. Or at least, feeling permanently financially comfortable.
But for some, the increased cost of living, maintaining a certain lifestyle and planning for the future can make them feel like their money is far from enough.
GOBankingRates spoke with millionaires Tommy Mello, entrepreneur and founder of A1 Garage Door Service, and Kyle Leman, CEO and founder of Crossroads Foundation Repair — who despite their riches, still consider themselves poor.
Staying Competitive Means Less Money for Personal Savings and Retirement
“As the founder of A1 Garage Door Service, a company that has grown to over $100 million in revenue, I’ve had the privilege of experiencing substantial financial success,” said Mello. “Yet, despite these achievements, there are moments when I feel unprepared for retirement and other future financial milestones.”
While this might sound contradictory, he said the nuances of wealth and financial security are more complex than they appear on the surface — running a large, successful business comes with significant financial pressures.
“To maintain and grow A1 Garage Door Service, a considerable portion of our profits must be reinvested back into the company,” he explained.
This includes funding for technological advancements, expanding their services and ensuring they provide exceptional customer service.
“Each of these investments is crucial for staying competitive in the market, but they also mean that less money is available for personal savings and retirement funds,” he said.
Economic Uncertainty Causes Strain
According to Mello, the economic landscape adds another layer of complexity. “We live in an era where economic uncertainty is the norm rather than the exception. Market fluctuations, unexpected expenses and potential economic downturns can have a profound impact on financial stability.”
He said these factors contribute to a sense of financial vulnerability, regardless of the wealth he’s accumulated.
“The cost of living has increased significantly over the years. … Healthcare expenses, educational costs for my children and maintaining a lifestyle that aligns with our values and desires all require substantial financial resources,” Mello explained. “It often feels like the financial goalposts are continually moving further away, making it challenging to feel truly prepared for future financial milestones.”
Planning for the Future Brings Its Own Set of Challenges
Taking care of his family — and providing his children with the best education and personal growth opportunities — is important to Mello, to “leave behind a meaningful legacy.” He added that balancing these long-term goals with the need to enjoy the present is a delicate act.
“It’s not just about accumulating wealth; it’s about managing it wisely and ensuring that it provides security and peace of mind,” he said. “Moreover, as an entrepreneur, there’s an inherent pressure to keep pushing forward, to keep innovating and to keep growing.”
This drive, while essential for business success, he said, can sometimes overshadow personal financial planning.
Prioritizing the Business Means Personal Financial Security Takes a Backseat
“The focus on the business often means that personal financial security takes a backseat, leading to feelings of unpreparedness,” said Mello.
Despite these challenges, he still believes in the importance of prudent financial management. “I regularly seek advice from financial advisors, stay informed about market trends and make deliberate decisions to balance business growth with personal financial security.”
However, he noted that the complexity and unpredictability of the financial world means that there’s always a level of uncertainty.
Wealth Accumulation Affects You Psychologically
“Despite being financially successful, I am not yet ready for retirement,” said Leman. “One of the many things that I have learned is how collecting wealth affects one psychologically.”
He said that, as his business grew, so did his “money distrust.”
“That’s odd, because the richer I became, the more afraid I was of losing it,” he said. “This process is not always given sufficient attention and can significantly affect one’s feeling of being well-prepared for tomorrow.”
Leman explained that the fear of loss paired with increased responsibility left him feeling poor. “The bigger the fortune, the louder the fear of losing it completely.”
He said this often leads to conservative financial choices that hold back development, and these abundance-related complications attract stress and doubts.
Lifestyle Inflation Is Also a Major Factor
“With higher earnings come greater expectations and costs associated with lifestyle change, making it difficult to maintain the same level of financial comfort during one’s entire life after retiring,” said Leman.
He noted that all of these conditions — fear of loss, increased responsibility and lifestyle inflation — create a financial vulnerability that makes long-term safety seem out of reach.
“These mental factors must be identified and addressed if financial preparedness and peace of mind are to be attained.”
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