M46 + F46] – Struggling to Spend Money Despite Being Financially Secure. How Do I Get Comfortable Enjoying It?
Hi everyone,
I’m 46, married, two kids (15 & 14). We’ve been diligent savers and investors for over 20 years — and now I’m realizing I might have swung too far the other way.
We’re in a great financial position, but I find it really hard to spend money on myself or even on things that would make life easier or more enjoyable. It’s like every dollar has to be justified or “optimized,” and I can’t seem to flip that switch off — even though logically I know we’re fine.
Income (Annual)
- My salary: $225K
- Spouse: $50K
- Business income: $45K
- Rental income (cash flow): $21.6K
- Interest/dividends: $10K
- Total: $351.6K (Unvested RSUs ~$1M not yet vested)
Assets
- 401(k)s: $1.5M total (mine + spouse)
- IRAs (Roth, rollover, solo): $245K
- HSA: $112K
- Brokerage: $1.9M
- Kids accounts (UTMA + ESA + Roths): ~$344K
- Savings/cash: $200K
- I-Bonds: $21K
- Rental equity: $275K
- Total investable (excl. home): ≈ $4.4M
- Primary home: paid off
Savings / Investments per Year
- 401(k)s, HSA, brokerage, UTMA, kids Roths , ESPP→ $160K/year saved
- Total expenses (family of 4, including travel, kids, parents, etc.): ~$113K/year
- That leaves roughly a $78K annual surplus.
The Problem
Even with this margin of safety, I struggle to let myself enjoy money.
- I hesitate to upgrade things that are old but “still work.”
- I overthink every nonessential purchase.
- Even vacations, hobbies, or dining out feel like “spending mistakes.”
- I’m aware this mindset came from years of saving and discipline — but it’s starting to feel limiting.
I’m not talking about blowing money or lifestyle inflation — more about being able to enjoy what I’ve earned without guilt or anxiety.
My Ask
For those who’ve reached (or are near) financial independence:
- How did you mentally transition from saving to spending?
- What helped you feel okay using your money for comfort, fun, or time-saving conveniences?
- Any frameworks, “rules,” or mindset shifts that made it easier?
- Did you find setting aside a specific “fun budget” helped, or did something else click mentally?
What I’m Trying to Work On
- Reframing money as a tool for living, not just a scoreboard.
- Accepting that my kids’ memories and my own comfort might matter more than optimizing every basis point.
- Learning that “enough” might actually mean… enough.
Has anyone else gone through this phase?
How did you start feeling okay with spending without guilt after years of saving?
Note: Using AI to cleanup my writing a bit and structure the post.
Advice Needed – Struggling to Reprogram My “Always Save” Mindset
byu/JohnBanaDon infinancialindependence
Posted by JohnBanaDon
5 Comments
I increased my non-essential budget by a couple grand per month, solved a couple smallish (<$10k) problems for family members including helping them get into school and then the real fun one was I just started happening to have extra rooms in Airbnb’s or extra concert tickets, or a celebration/dinner place that we have to try that I used for connecting with friends, family and even co-workers that maybe couldn’t justify it. I really had to work at getting used to spending the full budget….
It’s a great time to start making sure you and your spouses entertainment goals still align as you prepare for the kiddos to head off to college and the big shift in the households day to day flow once their off on their own…
I do buy stuff I want quicker now and just pass whatever I upgraded onto someone else, but most of the basic habits haven’t changed. Still picking up the generic food items or buying stuff that is on sale and sticking it in the freezer. Tried to upgrade my older cars but just didn’t see anything that fit the bill so waiting for that….
At this point in your life / kids life, I’d prioritize spending on experiences. That could be any number of things – travel, educational opportunities (beyond the basics), things that help your kids in their chosen passion (coaching, tutoring, camps, programs, etc.), fun stuff you can do locally as a family (concerts, sporting events, etc.). Time is the finite resource here as your kids grow up and begin to make their own independent lives.
Ramit Sethi’s book I Will Teach You to Be Rich is a good place to start. He preaches “spending extravagantly” on things you love and saving on the things you don’t.
Spend your money on experiences. As you get older you can’t or won’t do things that you could do when you were younger. So remember that and ask yourself would you regret not doing it. Take that holiday you said you were going to.
Buy that cool car and drive it ….trust me driving a Porsche or Ferrari at 60 plus is different to doing at your age. As you get older your reflexes slow down and things that used to work don’t work like they used to. Not saying you need to buy the flashy car or expensive things. But use the cash to do things that create experiences that you will remember and reminisce with family and friends.
Start small with a small holiday or purchase. Then go from there.
You have done well to build your wealth and financial security. Now enjoy it.
The great thing about FI is that you can afford to be sub-optimal. You’ve bought yourself freedom. Congratulations!
One exercise I’ve suggested to people is to set a fun budget and if you don’t spend the full amount that month/quarter, the remainder goes to charity so you can’t save it anyways. Either way the money will leave your wallet.
> What helped you feel okay using your money for comfort, fun, or time-saving conveniences?
Another thing you can do is calculate your hourly rate ($108/hr for you if I just count your $225k salary) and ask yourself “will this cost me less than $108/hr of my own time?” The answer is probably yes.
My primary measures of personal contentment are comfort and novelty/creating opportunities for joy. That means investing in comfort (bed/bedding, furniture, clothing), stuff that makes my life better (good cookware, step stool, organizational tools), exploring (trying new local restaurants and activities like ax throwing, salsa dancing, pottery classes), and my relationships (traveling to friends, spending money on hang out opportunities). That is what, when I think back to, gives me the warm and fuzzies.
The money doesn’t. It’s a means to an end and a good way to calm my anxiety, but the number going up on a spreadsheet doesn’t make memories or make me content with my life.