40 Over 40: Inspirational Money Wins at Age 40+

By Jackie Beck   Updated 03/21/2020 at 11:48 am

40 over 40 inspiring money storiesThink it’s too late to improve your financial situation? These 40 over 40 folks with inspirational money success stories prove it’s not!

Ranging in age from 40 to 63, these Gen Xers and Boomers took charge of their money and changed the course of their financial lives.

They’ve had all kinds of money wins at age 40 and beyond, including things like:

  • saving for retirement
  • becoming financially independent
  • paying off debt
  • retiring early
  • starting businesses
  • becoming location independent
  • and a whole lot more

Ready to get inspired by their money wins? Read on for the stories from these 40 over 40!


1. Kathy Lee

Ratcheted up retirement savings at age 55

Kathy Lee
6 years ago, Kathy’s husband nearly died and was unable to return to work. She realized that although they had gotten out of debt in their 40s, they didn’t have a big enough emergency fund and had very little put away for retirement. So Kathy got creative with ways to boost their retirement savings. She found a government job with a pension and a 457b deferred compensation plan that allowed her to catch-up retirement savings to the tune of $38k per year for 3 years! She maxed out her IRA & a spousal IRA, contributed to an FSA, and got another (higher paying) part-time job where the employer contributed to a SEP-IRA for her. She now blogs at Baby Boomer Super Saver.

2. Sebastian Rodrigues

Paid off his mortgage at age 52

Sebastian Rodrigues
Sebastian’s fascination with numbers helped him pay off his home by age 52. It took him just 12.5 years instead of the typical 30 years, and he saved tens of thousands of dollars in interest in the process. How did he do it? First, he looked into the difference between a 30 year and a 15 year loan, and discovered that the mortgage payment would not double. It only went up roughly 27% which he was able to afford, so he took out a 15 year mortgage. Then he decided to add an automatic $250 a month to his mortgage payment to pay it off even faster. Sebastian is a co-blogger at Money Saved is Money Earned.

3. Wendy Glover

Paid off $20,000 in debt at age 46

Wendy Glover
Wendy’s paid off $20K in credit card debt over the past year and a half, while also cash flowing legal fees. And she’s still going strong! Wendy is currently working on paying off her last credit card (number 10 of 10), and then will begin tackling her student loans.

4 & 5. Ali & Alison Walker

Retired at 44 & 54 to travel

Ali & Alison Walker
Ali & Alison reached financial independence when they were 43 & 53, and retired a year later from their careers in marketing and business development (Ali) and managing image retouching (Alison). They wanted a complete change, so they sold their car, Seattle home, and 99% of their belongings to travel the world. Says Ali, “Hitting FIRE at 44 and 54 felt great. And after 16 months of this slow travel lifestyle, we are still loving it! We are proud to be over 40!” They write about their adventures and their finances at All Options Considered.

6. Jessica Garbarino

Walked away from her 6-figure job at age 42

Jessica Garbarino
Jessica had a six-figure corporate job with full benefits and paid vacation — the kind of job she’d worked hard toward for her whole adult life. But at age 42, she gave it all up. The high-stress environment was making her health worse, and she knew she had to taking care of herself the priority. It helped that she’d put herself in the kind of financial position that meant she could afford to give her notice and quit without another job lined up. Now, she’s able to spend time with friends and family while being able to pick and choose the projects she wants to work on. Jessica is proof that taking the time and effort to improve your finances is well worth it. You can read more about her and her story at Every Single Dollar.

7. Karen Zee

Paid off all consumer debt and hit a high savings rate at age 59

Karen Zee
At age 59, Karen used the principles of financial independence to make a drastic difference in her life. Less than a year ago, she had about a 6% savings rate and about $30K in debt. Since then, she’s paid off all consumer debt using a debt snowball / debt avalanche hybrid and built up a moderate emergency fund. She’s now quickly paying down a final home improvement debt and paying a moderate additional amount on her mortgage — all on a base pay that’s well under six figures. She will max out her Roth 401(k) and company 401(k), including catch-up contributions this year and her savings rate is almost 60%. To do all this, she used strategies like house hacking, credit card hacking and balance transfers, reducing expenses, and taking a second job where she telecommutes. She lives a frugal life with minimal needs, and doesn’t want for anything important to her.

8 & 9. Jim & Courtney Robinson

Increased their net worth from from $0 to $600,000 by ages 61 and 49

Jim & Courtney Robinson
When Courtney & Jim met, neither one was making over $30,000 a year and they had 6 kids between them, including one who is disabled. Yet they were able to grow their net worth from $0 to $600,000 in 8 years. They did this by working 3-4 jobs between them to pay off debt (at multiple small businesses of their own, at regular jobs, and via side hustles like writing books about yoga), saving and investing, and living well below their means. They cash flow everything, both drive old cars, and never increased their expenses. They continue to live on $35-$53K a year, and are paying extra on their mortgage. That and sweat equity adds up, says Courtney. “It’s a combination of the little things and the big decisions along the way.”

10. Kassandra Dasent

Focused on financial independence at age 43

Kassandra Dasent
Kassandra Dasent, is a prime example of the sandwich generation. She’s immigrated twice, is a long-distance caregiver to her elderly mom in Montreal, and partially supports family members. After witnessing the financial struggles of family and experiencing her own battle with debt (she paid off $55K), Kassandra and her husband took the concept of financial independence and security to heart. “That my husband and I would have enough money to sustain us long-term should one or both of us need to retire early to due medical illness, or simply because we are tired of working, feels like the best gift that we can give to ourselves,” she says. At 43 they are now investing heavily for retirement and working to become financially independent. Based on their projections, they should reach FI in 7 to 10 years.

11. Brian Brandow

Paid off $109,000 in debt by age 45

Brian Brandow
Brian started his debt repayment journey at 40, after never having a plan for his money and overspending in his 20s and 30s. He & his wife had backed themselves into a corner with $109K worth of consumer debt. But they finished paying it all off by the time Brian was 45! “It was overwhelming at the start to cut up our credit cards, and work a budget,” says Brian. “It was something we had never done before. After serval months, budgeting became routine, and the stress of money was lifted. Along our debt repayment, we handle several bumps in the road, from the minor home repair, major car accident, surgery, and a job loss. These are all things that would have been financial disasters if we did not have a plan for our money.” You can read more about his story at Debt Discipline.

12 & 13. Vicki & Alan Thompson

Paid off their house at age 47

Vicki and Alan Thompson
Vicki & Alan gave themselves an amazing birthday present by paying off their house right at their 47th birthdays. (They were born 12 days apart.) Their original mortgage was $120,000 in 2002, and their house is now valued it maybe 240,000. Prior to getting out of debt, they’d gotten by just fine — if “just fine” meant treading water financially. But during their debt free journey they made real progress with their personal finances, moving forward as they paid off debt. (Before paying off their house, they became consumer debt free at age 41 by using the debt snowball to pay off about $37,000 in 13 1/2 months.) They pinched pennies, made sacrifices, and learned how to be generous. They kept right on going with their debt snowball until their house was paid off too! They’re now fully enjoying their paid-for house. “If I could put my arms around our house I would, it is a completely different feeling knowing that you actually OWN it,” Vicki says.

14. Miranda Marquit

Funding a run for office at age 40

Miranda Marquit
Miranda Marquit is a nationally recognized freelance writer who is also highly active in politics. She is funding a run for office in Idaho. Running for office often takes a great deal of both money and time. Miranda points out that “Even at the state level, a campaign can cost more than $10,000. If you take the time to run a good campaign and connect with constituents, you can reduce the amount that you pay for (or go into debt for) when running for office.”

15. Jackie Koski

Retired at age 49 after reaching financial independence

Jackie Koski
After overcoming poverty, divorce, and single motherhood, Jackie reached financial independence in her 40s, while making less than six figures and raising her daughter. She just retired early from her corporate job at 49 to follow her dream of creating a financial-literate society. And she did it decades before others told her she could. She learned everything she could about personal finance issues like credit, saving, investing, and other money matters early on. But going through divorce was a turning point for her, in that she was challenged to put her knowledge into practice. She openly shares how she overcame those adversities and climbed into the middle class on numerous podcasts, and in the book she wrote. Money Letters 2 my Daughter is a series of letters to her 17-year old daughter about all things dealing with money and personal finances.

16. Lisa Wimberger

Launched an institute at age 42

Lisa Wimberger
After experiencing multiple traumatic events, Lisa developed a meditation system to help. At age 42, she opened the Neurosculpting Institute where she shares practical and powerful stress management techniques. But she hasn’t stopped there. She’s written 7 books between age 42 and 46, opened a franchising business at 46 that now has over 60 franchises, and opened her newest company at age 50.

17 & 18. Trinity Montero & Bonnie Truax

Retired at age 43 to travel full-time

Trinity Montero and Bonnie Truax
Bonnie grew up living below the poverty line. She paid for college by working multiple jobs, and graduated debt free with a degree in counseling. Then she got married, inherited a bunch of debt, and divorced. She ended up working at an IT job, which is where she met Trinity, who was born and raised in the Philippines. He’d migrated to the United States with little more than a suitcase and an IT job offer. They eventually married and began living a very frugal life together, saving most of their money at first. At age 43, they realized they didn’t need to keep working 50-80 hours a week at insanely busy corporate jobs, and opted for early retirement. They bought a few foreclosures and rented them out. They’ve spent the past 4 years enjoying slow travel and volunteering, and write about their adventures at 43BlueDoors.

19. Jay Jermo

Started a business at age 40

Jay Jermo
After losing his job, condo, and savings, Jay made a move to Michigan. He was able to turn everything around by starting his own business in a completely unrelated field at age 40. With little more than $100 in his bank account and a display table for farmers markets, he created a specialty flavored honey sales company called Hey Honey. By his second year, customers were asking for his web address so they could buy the honey online. “I would not have been able to build this business in my twenties or thirties,” he says. “I really needed to reach the age of 40 to be in a place to completely restart a career from the ground up. My take-home income is now many multiples of what it has ever been in working for other people.”

20 & 21. David Auten & John Schneider

Became location independent at ages 47 and 44

David Auten and John Schneider
They’re currently living in Spain for a few months, and have traveled around the United States and Europe while running their business for the past two years. Their story starts when they were in their 30s, making good money as two financial services professionals. The only problem? They made a bunch of bad decisions too. They had fun unthinkingly going into $51,000 in credit card debt. But one day reality hit, and they came to their senses. After paying off that debt in less than 3 years, they started a business to help others avoid and overcome debt. (You can find them at DebtFreeGuys.com or listen to their award-winning Queer Money Guys podcast.) Eventually, they were able to quit their jobs. (John quit first at age 42 to focus on the business, and David followed later at age 47.) The final step was selling their house & becoming location independent.

22. DeShena Woodard

Became 100% debt free at age 49

DeShena Woodard
DeShena’s troubles with debt started during her first year of college, when she was approached on-campus by a credit card rep who encouraged her to apply. She loved feeling like a real grownup, and being able to buy items she didn’t have the cash for. That was the start of her spiral into debt. She soon added student loan debt and other credit cards to the mix. Eventually, she worked hard to change her mindset and improve her finances. After years of struggling with the misery and stress of debt, she paid off almost $52,000 in a little over 2.5 years and is now 100% debt free! She’s now actively pursuing FIRE. She shares her experience with others at Extravagantly Broke, a blog dedicated to empowering women to crush debt and pursue their passion.

23. Sydney Lagier

Retired at age 44 during the Great Recession

Sydney Lagier
Syd was a CPA who worked as a CPA and later landed her dream job as a controller at a venture capital firm. While there, she was able to sock away what she calls “the gravy”: the unexpected windfalls, bonuses, and other compensation beyond her normal salary. She tried out semi-retirement by working part time, but it didn’t really bring her the kind of work-life balance she’d hoped for. When her husband became unemployed when the dot com he worked at went under, she went back to full time work and he settled into retirement. 4 years later in 2008, she joined him in retirement. Prior to that, they spent five years building a solidly diversified portfolio, and stockpiled three years of living expenses for retirement in cash. A few years into her retirement, she was tempted back to work on a part-time consulting basis for two years, and enjoyed it. “Not only did I really enjoy that job,” she says, “I really enjoyed walking away from it. Because while I was working, I started to realize that I had taken a lot for granted that first go-around at retirement. I’ve been retired full-time again since August of 2012 and not taking anything for granted this time.” Now age 56, she blogs about retired life at https://retiredsyd.typepad.com/.

24 & 25. Steve & Annette Economides

Started a business at ages 45 & 42

Steve & Annette Economides
Now New York Times Bestselling Authors, at ages 45 & 42 Steve & Annette began work on their original goal: to write a print newsletter that they would eventually turn into a book. A little over a year after starting their newsletter, they got on Good Morning America — where they were dubbed “America’s Cheapest Family” — and got a book contract. They became best selling authors a month after its release. They’ve since written 3 books and created numerous products, and continue to run their business at ages 62 and 59. They love to help others with money saving tips as speakers and on their site Money Smart Family.

26. Wendy Mays

Got rid of $650K in debt by age 46

Wendy Mays
At age 45, Wendy and her husband got bit hard by the financial independence/retire early (FIRE) movement. They went from drowning in debt and feeling hopeless to inspired and taken action. While they aren’t yet totally debt free, they’re well on their way. They’ve paid off $110,000 in consumer debt. Wendy says, “That first year, we cut everything. EV.ER.Y.THING. We reviewed our bank statements and asked the question of every expense: ‘Can I reduce this expense?’ or ‘Can I eliminate this expense entirely?’ From there we began to systematically pay off debt while simultaneously reducing our household expenses.” They first tackled the debts they had with large payments that they knew they could pay off quickly, then moved to using the debt snowball method. Finally, they decided to go all-in and sell their house as well, which brought their total debt elimination to $650,000. By reducing expenses and debt, Wendy was able to retire her law practice and become a stay at home mom to their 6 kids. They’ve also increased their savings rate to 29% from a starting point of about 5-7%. “We know we can do this,” says Wendy. “We can be debt-free AND be financially independent by age 55.” You can read more of their story at House of FI.

27. Jim White

Retired at age 43

Jim White
Jim and his wife got married in 2006. After the birth of their daughter a few years later, Jim was determined to spend more time with her. He learned about the FIRE movement and pushed hard toward that goal for years. They reached financial independence and he retired at the end of 2018 at the age of 43. In the summer of 2019, he & his family moved to the country of Panama to try it out for at least a year, where they’ve been loving life together as a family. He blogs about their journey at Route to Retire.

28 & 29. Dylin Redling & Allison Tom

Retired at ages 43 & 44

Dylin Redling and Allison Tom
Dylan and Allison managed to pay off their mortgage and then retire in their 40s, all while living in the Bay Area. They both had decent jobs, but relatively modest salaries considering the high cost of living area. They did it by setting up automated investments, investing in real estate, and rental property, creating multiple income streams, and keeping their expenses down. They are now traveling and enjoying early retirement. You can read more about how they did it on their site.

30. Bobby Warren

Started a business at age 55 and increased his income by 41%

Bobby Warren
After three decades studying and working in journalism, Bobby struck out on his own at age 55. He started a search engine optimization/content creation business called Wooster Media Group after getting inspired by Claudia Pennington at a blogging conference. His wife Wendi supported the move, even though his last foray into launching a business failed miserably nearly 20 years ago. This time he knew he needed to earn at least half his reporter’s pay the first year, and the family would be OK. So he launched the business and earned close to 75% of his pay that first year. In year two, his business grew, earning 41% more than his last year at the newspaper. Because of the growth of Wooster Media Group, his wife left her full-time job to join the business. While the couple would have liked to use the extra money to eliminate debt, it helped them pay cash for a new roof, a new front door, and a lot of car repairs.

31. Cameron Huddleston

Got a book advance at age 45

Cameron Huddleston
Cameron Huddleston learned firsthand how hard and important it is to talk with your parents about their finances when her mother was diagnosed with Alzheimer’s at age 65. Cameron knew she needed to prepare to make all financial decisions for her mother. But she didn’t know anyone going through the same thing, and resources were lacking in the area. So Cameron put her life experience with her mother and her experience as a journalist who writes about personal finance to work. She got a book deal at age 45 and her book, Mom and Dad, We Need to Talk was published when she was 46.

32. Deanna Broaddus

Paid off $46,763 in debt at age 44

Deanna Broaddus
Four years into her recovery from drug addiction/alcoholism, Deanna felt ready to tackle the problems with her financial life. She learned from Dave Ramsey’s radio show and got to work on the baby steps. She built an emergency fund and started her debt snowball. Unfortunately, she lost a house to foreclosure in the process. But she bounced back by making some extreme choices in her life. For example, she moved in with her parents at age 42 so she could focus on paying off her remaining debt. By age 44, she’d paid off her $46,763 in debt on a mediocre salary. Along the way, she went from earning $40,000 a year to $60,000 a year and learned to become an investor. Now age 47, she’s on the path towards financial independence. You can read more about Deanna at Recovering Women Wealth.

33. Vanessa Lowe

Reached $1 million in retirement savings by age 54

Vanessa Lowe
Vanessa has had several big financial wins. She paid off $78,000 in grad school debt by age 42, built a 3-year emergency/opportunity fund by age 48, and of course amassed just over $1 million in retirement savings by age 54. She says that while her journey hasn’t been fast, it’s been consistent. For her, the key to it all was sticking with a pure US stock retirement portfolio, maintaining that throughout the downturn, and never borrowing from the retirement account. She did all of that while working first in the legal services non-profit sector, then briefly in the private sector, and finally working in federal service supporting access to capital for underserved communities. You can learn more about Vanessa at her site, VLL Consulting.

34 & 35. Amy & Tim Rutherford

Became “home free” at ages 51 & 52

Amy & Tim Rutherford
Tim and Amy were able to retire in their 40s by cutting back on spending and shifting their focus. Says Amy, “We made a conscious choice to delay gratification. Our journey along the way was incredible but we were well within our boundaries. I took off 5 years to raise the kids (3 from Tim’s prior marriage). When I returned to work, every single penny I earned was saved. No exceptions.” Since then, they’ve been spending their time traveling and house sitting. But they went a step further this year when their youngest child became an adult. They realized it didn’t make sense to maintain their paid off home due to the $1000 monthly expenses of taxes, HOA dues, insurance, and utilities. So they let go of most of their possessions and became “home free” this year at ages 51 and 52. They’ll sell their 2008 car in May as well when they head abroad. They plan to be out of the US for 10 months a year going forward. You can follow their adventures on their YouTube channel or learn more about them on their site, GoWithLess.

36. Becky Heptig

Turned her money situation around starting at 50 and retired at 63

Becky Heptig
Becky & her husband’s financial situation was never the greatest in that they hadn’t saved for emergencies, kids college, or retirement. Then their money situation got worse when two of her husband’s clients decided not to pay them. It was an awful time in their life. Then things started to turn around. Eventually her, husband got a job and her kids got scholarships. They knew they never wanted to be in that position again, so paid off debt and began saving everything they could. Then one of their sons introduced them to ChooseFI podcast. They learned more, put what they already knew into warp drive, and made retiring earlier than planned a priority. By doing so, they cut 3 years off their time frame and were able to retire at 63. You can read more about Becky & her husband’s story at Started at 50.

37. Bobbi Olson

Paid off just over $60,000 at age 44 and hit a positive net worth


Bobbi paid off just over $60,000 in 5 years, with a $60,000 household income. She had been paying a little over the minimums of each debt for a while, but wasn’t really getting anywhere and had the belief that she’d always be in debt, so she was more focused on not incurring any new debt. Then she read The 60 Minute Money Workout by Ellie Kay and learned about the debt snowball method. In trying to prove Ellie wrong, Bobbi learned that it could work for her family, created a plan and followed it. After that, she started reading everything she could get her hands on to learn more about budgeting, saving & paying off debt. It became a passion, and she now writes and podcasts about money at CentsAble Chat. Bobbi says, “The biggest struggle was sticking to the plan when we wanted to go out to eat, or turning down friends who wanted to go to concerts or expensive dinners, because we were on a budget. But it was certainly worth it! Now, we’re debt free and on to wealth building! Honestly, it’s been slow, because unexpected things keep popping up that need to be paid for, but now we can pay with cash, instead of incurring new debt! Life is good!”

38 & 39. Pierre & Jaime Gibbs

Starting saving for retirement in their 40s

Pierre and Jaime Gibbs
49 year old Pierre and 43 year old Jaime Gibbs are living below their means so they can hit some big savings goals. “Now that we’re past 40, it seems more urgent to save money rather than spend it,” says Jaime. They are saving aggressively for retirement: maxing out Pierre’s 401K (with catch-up contributions since this is the year he turns 50), contributing to Jaime’s solo 401K, maxing their HSA, and also contributing to an after-tax investment account. To get to this point, they paid off debt (including their current house), downsized, and got good at working a budget. (Jaime’s site is Bubbling Brook Budgets.) They’ve increased their income while keeping their expenses low so they can save more. They are currently at about 25% of their goal and plan to reach 100% within 5-10 years.

40. John & Amy Blacklock

Paid off $65K and reached a 7-figure net worth by ages 49 & 50

John and Amy Blacklock
Amy stumbled across Mr. Money Mustache and the FIRE community at the age of 45 and it completely changed her life. She and her husband paid off all non-mortgage debt ($65,000) in 3.5 years and aggressively saved and invested for retirement. Through pulling many different levers ourselves – cutting expenses, earning more, saving more, and investing – plus a great stock market, they were also able to triple their net worth to seven digits in six years. Amy was able to leave her full time job two years ago at the age of 49 to devote herself to family and passion projects like Life Zemplified. John will will retire within the next couple of years, 10+ years earlier than he originally thought he could.

Did you find this 40 over 40 article inspiring? Share it with a friend or on social media! And if you’d like more inspiring stories, check out these debt free stories as well.

4 thoughts on “40 Over 40: Inspirational Money Wins at Age 40+

  1. These are great stories. We didn’t get serious about FIRE until after 40 and still managed to hit our leanFIRE number still in our 40’s. Regarding over-40 money achievements, I would also put big career wins in there for people who want to stay in more traditional careers but feel discouraged by mass media coverage of age discrimination. Here’s one success story: 50-year old gets laid off from one job, but still makes a career change with a higher salary and title within 3 months: https://www.forbes.com/sites/carolinecenizalevine/2018/06/09/from-layoff-at-age-50-to-a-career-change-and-promotion-within-three-months/

  2. Thanks so much for this! As a 47 year old single mom struggling with six figure debt (mostly student loans), I am completely discouraged and resigned because most of the financial freedom success stories out there are either from young people or from couples. It is good to see people not unlike myself represented and know that it is never too late to turn around a bad financial situation. Please do more of these!

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