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How I Went From Underearning to Six Figures in 5 Years

I’m nearly 40 years old and have spent most of my adult life as an underearner. This happened because I had no career path as a young adult (ages 19-21) and then worked a job that paid poverty-level wages until I was 26. For a short time (ages 26-29), I reset by going to college while my wife worked, and I took care of our home and kids. After graduating, I started from the bottom of the ladder as a federal employee and worked in an entry-level position. After some initial advancement, I foolishly assumed that hard work alone would solve my financial problems, and soon enough, I’d be an author making plenty of residual income.

But I quickly learned I was wrong.

It wasn’t until I changed everything about how I approached my career that I was able to drastically improve my financial circumstances.

My Journey to Earn More

As a US Marine with a family, my pay qualified me for multiple forms of welfare, and even as a Sergeant I received the Earned Income Tax Credit. In 2008, my take-home pay, including a housing allowance to live off base, was $3,000 per month.

When I left the Marine Corps, I was already in college and had been rated as 60% disabled for various injuries that went nearly from head to toe.

Financially, working any job for the rest of that year (2008) would have actually cost me money because I was receiving roughly $4,300 per month between my VA pension, unemployment, and the GI Bill – 1.4x what I’d made as a Sergeant.

The local employment office referred me to some open positions (furniture sales and Starbucks are the ones I recall). A private security company offered me $8,000 per month to go to Iraq. A few years later, a defense contractor offered me $12,000 to go to Afghanistan.

Because I knew the true psychological and financial math – I also knew to say no.

I finished my associate’s and bachelor’s degrees while trying to create enough income from writing not to have to get another job. But that didn’t work out, so I got an accounting job and started at the bottom.

After getting my bachelor’s in marketing, I was hired by the IRS to be a seasonal tax examiner and then accepted a position with a small accounting firm. I didn’t mind the former but hated the latter. I was then hired to work at a factory. It was nice to work somewhere where we made things other than money; if I could make a difference, it would help all the families who depended on the company staying open. Shortly after that, I became the Chief Marketing Officer.

The accounting firm and factory were family-run businesses. The truth is that if you’re not family in a family business, you’re not anyone. That can even go for relatives who aren’t deemed close enough.

Although, in both cases, I wasn’t technically family –I was treated as such because I grew up knowing both CEOs and their kids. Those relationships got me in the door, but when it came to getting paid, it still wasn’t enough.

At the accounting firm, my salary was $39,000, and I quickly learned that they wouldn’t reimburse me for lunch unless I were taking out a client in a way that I could bill him. So, while I made them $800 on days I went to New York City, I had to pick up my own $8 sandwich.

At the factory, my salary as CMO was supposed to be boosted by 4% of the sales I brought in and a bonus on customers I managed. Promised commissions never came. The last straw was after I’d brought in Wal-Mart, and my boss said it would be a “house account,” meaning I’d get nothing.

To this, I had to choose from burning the place down, resigning, or operating a remote second job from my office so that I could make my bills. I had bought a house and needed the extra income that I thought all my travel and sales were going to bring in. I chose the third option and will talk about that in a bit.

From 2011-2012 I was an IRS Tax Examiner. This position paid about $40,000 a year, but it was seasonal, meaning subject to furloughs. I was furloughed 3 times.

I worked as a public accountant from 2012-2013. The $39,000 salary was steady, included a bonus, and I was told I was on a partnership track, which seemed believable when I was the point person to very important clients. Unfortunately, it ended up being an extremely toxic work environment, and I was treated like garbage. I gave them the courtesy of 3 months’ notice (offering to work through tax season), and then I left on April 30, 2013.

The factory I worked for from 2013 through 2016 paid me a salary of $45,000, but the real appeal was that there might have been an opportunity to buy the company. I was very open about my goals, and the owner said it could be possible. None of the owner’s children wanted it, and he claimed that the sole relative (the VP) working there wasn’t worthy.

I quickly got the company a grant from the SBA and received a small commission. This led to a discussion about other ways to increase my income while growing the company. I brought in another grant, tried to enact programs that would save money, and attained several new high-value accounts while managing several others. But no additional income ever came, save for a small raise to my base salary.

After more than 2 years of being unable to make any real changes and not receiving promised commissions, I realized it was time to move on. Although disappointed and frustrated, I kept things professional and opted to tell any coworkers who asked that I’d gotten an offer that was too good to pass up.

The job that was “too good to pass up”? It was the one I’d gotten in 2011 as a seasonal IRS Tax Examiner. I took it. Then they furloughed me.

Upon returning, I saw a job posting for recent graduates. I’d finished my MBA that May, so I applied. And so, in 2017, I was hired as a chief counsel paralegal. At age 35, my salary finally exceeded $50,000. After a year, I would either be promoted or let go. When this time came, my salary was increased to $69,000. Another year later, my salary went up again to $72,000.

I got the word in October of 2019 that I had been selected for a promotion. The pay was $89,000 and allowed me to work remotely 4 days a week, adding 25 more nights of sleep to my year. Rather than being in an interior cubicle, my office would overlook Eisenhower Park.

By January of 2021, my pay had been raised to $92,000.

I received an annual review in May, then began applying – 60 positions in 6 months. The results yielded 5 interviews, and I then received a no-interview offer with an imminent start date. I accepted.

On November 22, 2021, I logged my first hours at my new job as a tax policy analyst with an annual salary of $106,500. With the new year, it bumped up to $109,690.

My professional objectives now are simple: Do a good job, and apply for promotions like mad after getting an annual review. If the offer comes from the team I am with, I’ll stay, but I’ve set my site on a Senior Executive Service position, so I need to continually advance.

Don’t Be Afraid of Failure

At nearly 40 years old, I am now Partial FI. It does help our finances that we do things like keep our cars as long as we can, but both of us having VA pensions and GI Bills made a huge difference. I have also generally kept a second job and various projects “in the works” to bring in additional income. I’ve done everything from private security to driving for Uber.

Not all my efforts ended in success, but I learned valuable lessons and was able to hone my marketable skills through these experiences. You can’t be afraid of failure on the journey to FI.

Why I’ll Regularly Apply for Promotions

My professional methodology has many personal, professional, and health considerations.

When I made half as much, my life was twice as hard. Having tough times at work was always balanced by wonderful home life, but putting up with corporate politics and doing everything I could to get ahead without getting much in return, isn’t a bridge I care to cross again, much less reinforce.


By waiting any amount of time to strive for a higher position, I’ll reduce my lifetime earnings and long-term retirement savings. Regarding the latter, I get a 5% match, and the difference in investments can be found in the table below, which shows a modest annual return of 7%:

SALARY & YEARLY INVESTMENT TOTALS (5% of income plus a match)

Year 1$4,173$5,885$7,383$9,844$11,556$16,050
Year 5$22,786$32,134$40,313$53,751$63,099$87,637
Year 10$54,386$76,698$96,221$128,295$150,608$209,177
Year 25$248,056$349,823$438,868$585,158$686,924$954,062
Year 35$541,848$764,144$958,654$1,278,205$1,500,502$2,084,030
Year 40$782,398$1,103,381$1,384,242$1,845,656$2,166,639$3,009,221

* The math on this is not exact. It accounts for the numbers as though lifetime salaries are flat and contributions are made in a lump sum. But the principle is what needs to be considered. Your low salary impoverishes you for life and kills your chances of growing wealth because as soon as you’re eligible to withdraw your investment savings, you need the money for yourself or a loved one. If you intend to retire with a higher position (salary), get it now, not later.

But this isn’t the whole story. As a settlement officer, I began investing about 15% ($500 per paycheck) into retirement before the match – taking home the same as before while investing the pay raise for later. The table above does not reflect this; the additional difference is in the hundreds of thousands.

The years that matter in terms of career are the early ones because those can be pretty dismal if you don’t move up. For retirement, they are the 25, 35, and 40-year marks. 25 years from the point that I re-joined the federal service, I’ll be able to draw from my retirement savings. However, what if I leave the money there for another 10 years? Even if I don’t add to the account, the principle will double if it garners a 7.2% return.

However, that last part is a rich man’s game. If my income is low, I’ll need the money to buy essentials like groceries and pay for transportation costs. Or I might need it because I’m sick; don’t forget that poverty and poor health have been directly linked. That means that even in retirement (if possible), I’ll still be living paycheck to paycheck.


Do not overlook illness! Despite living an extremely health-conscious lifestyle, I am not as healthy as I once was. At nearly 40, I’ve had health issues creep in for brief periods, including migraines, hormonal imbalances, nausea, and a hand tremor. I’m lucky that these problems were all fixable, but I’d have been stuck where I was if they weren’t. After all, how high could I rise while constantly fighting chronic illnesses and conditions that held me back?

The Bottom Line

To optimally gain promotions, you need to apply like mad. I stopped caring about getting jobs I wanted and barreled out like a cannonball, not knowing where I’d land or caring.

If you work in the private sector, you might have to leave your company to move up, and then to move up again, apply outside of that company, possibly even to your former employer. If you work for Pepsi, see what Coke has to offer. If you’re an auditor at PWC, it might be time to run the accounting department at a hedge fund. And if you’re a top cashier at Whole Foods but hate being on the register, I bet any other grocery chain would be thrilled to let you fulfill a different role – be it assistant manager, the deli, or in the back handling shipments.

If you work in government, relocation can be the key. I had a friend go from NY to CA to MD. His old boss in MD had been in that role for 30 years, meaning that the only way to move up was to apply elsewhere. My friend was aggressive early and moved to wherever the next opportunity was. His early jumps boosted his lifetime income (and retirement savings), and he’s doing well.

Then there are those in federal service who will not get promoted because they either won’t apply or are waiting for the right position with the right agency. Others, it seems, are waiting for some sort of permission or sign.

For those waiting for that permission or sign, consider this it:

Stop doing the current job you hate that isn’t paying all your bills and has a toxic environment that’s making you miserable. Get serious about finding a higher-paying one that provides a good working environment to spend your day in and around. It’s time to prioritize and optimize your career trajectory. If that optimization involves getting promoted, then you need to get aggressive.

About the Author

Christopher Pascale is an author, accountant, and professor from Long Island. He is the author of War Poems: A Marine’s Tour, 2003-2008, and is currently writing a biography about Vice President Charles Curtis. His personal finance writing has appeared in print and online, and he edited The Golden Albatross (Choose FI Media) and Making Marriage Work (Rowman & Littlefield).

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