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AUTHOR: D.J. on 5/21/2026

Upon graduating in the early 1990s with a degree in English, folks would routinely ask: “Are you gonna teach?” That wasn’t in my plan, though. Instead, I landed an office job as a writer at a major magazine. The pay wasn’t great, but I could say I was a professional writer.

While there, I became eligible for my very first 401(k), administered through Vanguard.

Lucky for me, around that same time, Human Resources brought in a financial advisor to meet with my department, explain a few investment principles, and answer our questions. Just what is a mutual fund, anyway?

Following the meeting, I heard tales of woe from my editor and bureau chief. Both had lost noteworthy sums in personal investments that performed poorly. On the other hand, they spoke glowingly of the 401(k) and the Vanguard funds that were available in it.

The 3% matching contribution made by our employer further sweetened the deal.

I was hooked. From day one I contributed 15% of my pay, investing 10% of that in the Vanguard Prime Portfolio money market fund, 30% in Vanguard U.S. Growth Fund, and 60% in Vanguard Windsor II stock fund.

I don’t recall why I skipped the indexes and chose that mix all those years ago, but it’s a very different approach than I use today. I do know that although the two stock funds were broadly grouped as “domestic equity,” U.S. Growth and Windsor II at least had different investment styles, with Windsor II being more value oriented.

In addition, back then I found bonds confusing and didn’t yet grasp their place in a portfolio. I probably figured stashing some cash in the money market fund would suffice in terms of helping me sleep at night. In hindsight, 100% in stock funds would have worked out well. Live and learn.

As I moved into more lucrative work a few years later, I looked to Vanguard to start a taxable account. Seeking tax efficiency and long-term growth, I considered Vanguard’s 500 index and total stock market index funds. I eventually went with the latter given the wider market focus and minimal difference in performance. I’d also add a Roth IRA to the mix once Roths became available.

Regardless of where I worked, how much I made, or the 401(k) administrator, I always participated and paid myself first. My contributions never dipped below 15% and I leaned heavily on the lowest-cost funds available in the plan: usually broad-market index funds.

The 401(k) experience opened a new chapter in my life and helped me develop the confidence to later invest in the taxable brokerage account and Roth IRA. Having tax-deferred, taxable, and tax-free savings should provide flexibility when I turn the page to retirement.

No, this English major never became a teacher. But thanks to that first retirement plan and the spark it provided, I sure learned some valuable personal finance lessons.

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17 Comments
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Andy Morrison
1 month ago

I may have asked this before, but has someone run across any literature that discusses an optimal mix percentage of taxable/pre-tax/Roth?

Randy Dobkin
1 month ago
Reply to  Andy Morrison

I’ve not seen any, but here’s my take. Plan to leave enough in pre-tax to fill the lower brackets with withdrawals for the rest of life. Convert the rest to Roth (filling low brackets), having just enough in taxable to pay the tax on conversions.

Andy Morrison
1 month ago
Reply to  Randy Dobkin

Randy,

Interesting take worth consideration. Do you consider lower brackets to include up to 12% or 22/24? Maybe is driven by just how large one’s pre-tax accounts are before one embarks on the Roth conversions before RMDs?
Thanks for weighing in.

Last edited 1 month ago by Andy Morrison
Randy Dobkin
1 month ago
Reply to  Andy Morrison

Yes, either 12 or 24% depending on income, which in turn depends in part on taxable and pre-tax balances.

Andy Morrison
1 month ago
Reply to  Randy Dobkin

Got it, thank you.

William Dorner
1 month ago

You are very fortunate to have made the Vanguard and Index Fund decisions early in life. I try to teach my Grandchildren two things, Compounding and Inflation. Start saving early, take the max match, and Retirement will be some of your most enjoyable years. I dumped bonds about 20 years ago and now use mostly indexing with VOO and 15% cash to tide me over when the market takes a rest. My Dad taught me to always save something, and it stuck, and over 58 years, the market for me was only negative 9 losses and 49 positive wins. Nice, now I am spending our worth on my Family.

Kenneth Tobin
1 month ago

reading bogle and malkiel will make you investing gurus. its that simple

Edmund Marsh
1 month ago

Your story of slowly moving toward indexing is similar to mine, D.J. I started a little later in life, however, which necessitated a larger chunk of my pay going toward retirement, to wind up with enough.

Thanks for posting your story.

Dan Smith
1 month ago

DJ, I think it’s pretty rare for a young person to do things correctly, right from the  start of their career. Your story supports the contention that it is possible to pay yourself first, even when dealing with a modest starting salary. 
I recall someone around here arguing to save first, and live on what’s left. You did just that!

David Lancaster
1 month ago

DJ, did you read any writings of John Bogle back then?

Mark Crothers
1 month ago

D.J., respect — your story is a perfect example of prudent retirement saving. I also started young and contributed consistently over the years. And while I understood stock diversification, my downfall was not grasping tax diversification until much later in life. I should have spread money strategically across taxable, tax-deferred, and tax-advantaged accounts. I ended up with far too much in taxable accounts as a result. But I guess it’s a nice problem to have!

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