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Starting Up – Part 2

Andrew Clements  |  May 14, 2026

By the early 2000s, our business was heavily tied to the hotel industry, though over time we had added apartment complexes and office buildings to our customer base. When 9/11 happened, we suddenly felt exposed. Travel slowed, hotels struggled, and uncertainty was everywhere.
Then something unexpected happened. The Vice President of Operations for a major hotel brand called me personally and said, “Don’t panic. We’ll get through this.”
And somehow, we did.
My divorce became final in 2004.

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First Job, Lasting Impact

D.J.  |  May 14, 2026

In the spring of 1985, at age 16, I got a work permit and landed a job scooping ice cream at $3.60 an hour—slightly more than the state’s $3.35 minimum wage.
Before then, I brought in cash by mowing lawns, cleaning rain gutters, and selling the Sunday papers (yes, Los Angeles had two major dailies back then). But with a car and college on the horizon, I wanted a stable income.
I kept my job search within walking distance of home,

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Writing a Book in Retirement: The Good, the Hard, and the Surprisingly Meaningful

mllange  |  May 13, 2026

Over the past few years of retirement, I’ve discovered that writing a book is one of those pursuits that sounds serene from a distance—like a person sitting at a desk with a cup of tea and a head full of ideas—but in practice feels more like a long hike with stretches of beauty, stretches of slog, and the occasional moment where you wonder why you ever left the house.
I’m curious how many others here have taken on a writing project in retirement,

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The Rent is Too Damn High!

Michael Flack  |  May 13, 2026

RENT, n. 1. A regular payment made by a tenant to a landlord for the use of property. 2. An amount of money earned that exceeds that which is economically or socially necessary.
When I became of age, after becoming thoroughly familiar with the legal drinking age in New York state, I quickly became familiar with the first definition. A decade later after obtaining an MBA, I then became familiar with the second,

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My Recent Fill-up

Michael01670723  |  May 13, 2026

I filled up the gas tank this morning and the total was over $81. I drive a 4-Cylinder Chevy Camaro. Chevy recommends premium fuel – I use the mid-grade.
Still, that’s a record for me. So, I started to reflect…
When I turned 16 in 1973 I applied for a job at a gas station/car wash. It was owned by my best friend’s dad. I hired in at $1.25 an hour. which bumped up to $1.40 after the first 40 hours.

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Best method for buying home for permanently disabled daughter (SSI and ABLE account)

Dianne Baumert-Moyik  |  May 13, 2026

My husband and I are embarking on an effort to identify a small home to purchase nearby so his adopted Latvian daughter (my stepdaughter) may begin living independently at 33 years old. She has permanent cognitive disabilities that impact her attention and executive functioning but she has learned how to drive and remains gainfully employed part time.
We set her up with an ABLE account via ABLE United here in Florida so that she can work and save beyond the Social Security Supplemental Security Income (SSI) cap of $2,000 in assets.

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Help for divorcing daughter

dkkmc@aol.com  |  May 13, 2026

My almost 47 year old daughter is getting divorced from her 49 year old retired military  husband. He wants her to drop the Survivor Benefit Plan which costs close to $400 monthly and he will get a 15 or 20 year term insurance policy for $500,000 for her benefit. She has been a stay- at- home mom so her career prospects are unclear.  My concern is she could end up at 62 or 67 without the insurance or survivor benefits. 

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Retiring before age 65? COBRA vs ACA plan- important decision

R Quinn  |  May 13, 2026

For people retiring before age 65, obtaining health insurance is often a major concern.
The near automatic choice for many people is COBRA which allows them to keep their current coverage for a period of time. Generally 18 months if you lose your job or employer coverage. Other situations extend coverage longer or until Medicare eligibility and a few states also extend the 18 months for insured plans. Not all employers use insured plans and thus are not state regulated. 

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HumbleDollar’s HumbleDrivers

Dan Smith  |  May 13, 2026

During my days running union meetings, there was a thing called “for the good and welfare of the members”. Today’s post is about the good and welfare of HumbleDrivers.
In the past few weeks, two of my retired friends have complained that the ‘blind spot’ warning device on their new cars was useless. Both said that the yellow warning light on their side view mirror did not illuminate until a vehicle was approximately at their rear bumper.

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Tax Season Wrap up

Rick Connor  |  May 11, 2026

I recently completed my 8th season performing volunteer tax returns. I’ve worked in 2 states (Pa and NJ), 3 counties, and 7 centers. All but one year was performed under the auspices of the AARP TaxAide program. In several years I also worked for a local program supporting the Division of Aging and Disability in Cape May County, NJ.
This year’s location was at a local library in Monmouth County, NJ. The center was open 3 days a week.

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Direct Indexing Anyone?

ostrichtacossaturn7593  |  May 10, 2026

Do any HumbleDollar readers use direct indexing? (If you have to ask what that is, you are not likely using this.) If you are either using this relatively new financial tool, or if you seriously considered it and made a reasoned decision not to use it, I’d appreciate hearing from you.
My personal situation is an overallocation to cash (55%) caused primarily by selling out of a low-basis ETF that created an overconcentration in tech stocks.

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Benefits Young Adults Should Look at Before Taking a Job

Jeff Peck  |  May 10, 2026

Young adults entering the job market often focus on the salary or hourly wage first, and that makes sense. Pay matters. But the benefits package can be just as important, and sometimes a slightly lower-paying job with stronger benefits is actually the better deal.
Health insurance, deductibles, retirement matching, vesting rules, paid leave, sick time, disability coverage, tuition assistance, promotion potential, and work-life balance all have real value. A 401(k) match, for example, is part of your pay.

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When a One-Time Rental Sale Triggers an IRMAA Surprise

Jeff Peck  |  May 10, 2026

My understanding is that IRMAA is not permanent. It follows the two-year lookback. A friend and I were discussing the possible sale of his rental property, and that raised the question of what happens if a one-time capital gain pushes someone into a higher Medicare premium bracket.
From what I understand, if someone sells a rental property and has a one-time income spike, that higher income may show up in Medicare premiums two years later, but it should eventually fall back down once a lower-income year becomes the lookback year.

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The Mirrored Funnel

Mark Crothers  |  May 10, 2026

I was at our local annual civic parade and town carnival yesterday. One of those days we’d planned well in advance, arranging to take the grandkids and meet up with some thirty-something friends who also had young children in tow. It turned out to be a wonderful day. Vintage car rallies, a fairground, plenty of food stalls, live music, and costumed performers all doing their bit to keep the crowds entertained.
I’m a bit of a people-watcher at the best of times,

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The never ending payday

R Quinn  |  May 9, 2026

While working, there is something we call payday, it may happen once a month, more likely two or four times a month. Generally that means money is deposited into our bank account – a steady income stream we count on to pay a new set of bills. 
Then we retire and everything changes, no more payday. To me recreating that is the key to a less stressful retirement.  I can say that because I am fortunate to be able to do so and know the feeling of a retirement payday. 

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