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    You are at:Home»Side Hustle»Seven Tax Issues Distinct to Millennials as Identified by a CPA
    Side Hustle

    Seven Tax Issues Distinct to Millennials as Identified by a CPA

    administratorBy administratorFebruary 27, 2026006 Mins Read
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    Ah, millennials — the generation that’s somehow expected to juggle mortgages, college tuition, and elder care while still making avocado toast Instagrammable. It’s like trying to plate a five-course meal on a skateboard. Yet, here they are, managing to flip pancakes and stifle existential dread all at once.

    Despite the auctioning off of their sanity and the nostalgic longing for simpler times (when “adulting” meant choosing between cereal brands), millennials are proving to be a frugal bunch. Armed with resourcefulness and a Wi-Fi connection, they can tackle any financial conundrum that comes their way. And now, let’s dive into the tax concerns that keep them up at night — likely with a latte in hand.

    To channel the wisdom of finance mystics, MoneyLion consulted Kevin Golden, CPA and partner at James Moore & Co. “Many millennials are buying homes, building businesses, and starting families,” he mused. “But they’re also standing at the crossroads of tax opportunity and confusion. Think of it as a financial Schrodinger’s cat.”

    1. Juggling Income Streams Like a Pro

    Millennials have evolved into the side hustle elite, effortlessly sprinkling extra income streams like confetti at a wedding. Whether it’s from freelance gigs, digital ventures, or renting out that spare bedroom (not to be confused with a relative’s couch), each dollar comes with a tax twist.

    “Each type of income is like that quirky friend who shows up with a different dish at potluck,” Golden explains. “Self-employment income demands an extra dose of payroll tax anxiety, while investment funds might treat you to capital gains surprises.” So, while side hustling is the cool thing, hopping on a tax strategy is essential; otherwise, you might miss deductions like you miss the last bus on a rainy night.

    2. Student Loans: A Not-So-Secret Ingredient

    Student debt — the gift that keeps on giving, like a horror movie sequel that never ends. This debt doesn’t just shadow their financial decisions; it throws a wrench into the tax process, too. Watch out for inconsistencies, as they can trip up even the smartest millennials.

    Golden advises a keen eye for the kind of stuff that triggers nightmares: student loan interest deductions, income-driven repayment plans, and employer benefits to help ease the loan load. “Changes in income can affect eligibility for forgiveness programs,” he says. “But don’t forget to coordinate your finances like a symphony, or you might find yourself playing out of tune.”

    3. Homeownership: The Double-Edged Sword

    Ah, the dream of homeownership! Millennials have swapped their Dawson’s Creek memorabilia for homes with names that probably sound better than their last three relationships. The question now is: does having a home equal tax savior, or is it just another trapdoor in the labyrinth of financial escapades?

    Golden cautions, “Thanks to the higher standard deduction, many homeowners aren’t reaping the tax benefits they imagined. That mortgage interest isn’t the golden ticket anymore.” But fret not, aspiring landlords; if you’re investing in rental properties, plenty of nuances await, from depreciation deductions to passive activity rules. Think of it as being in a reality show where the winners get tax breaks.

    4. Remote Work and State Tax Shenanigans

    What’s better than working in your PJs? Working from anywhere! However, this isn’t just a lifestyle upgrade; it comes with its own set of quirky tax challenges. Golden notes, “Living in one state while working in another? That’s a tax Rubik’s Cube waiting to be solved.”

    #ProTip: Forgetting to update your tax info after a move could lead to a delightful mess of multi-state filings. It’s like accidentally sending your Christmas cards to last year’s address. You might end up paying double the state taxes, and nobody wants to be that guy. Review your state residency status annually — no one’s watching, but the taxman always is!

    5. Retirement Planning: Because Aging is Inevitable

    Retirement isn’t the distant future to millennials; it’s more like that raccoon outside your window — a constant yet curious presence that might even nibble at your trash. And yet, Generation Y is faced with what feels like a million retirement account options. Traditional? Roth? The choice feels like picking a favorite child.

    Golden wisely advises weighing the pros and cons. “Contributing to a Roth when you’re in a lower tax bracket could be a disaster for your wallet in the future — if you play your cards right.” Understanding your current income and future expectations can help you strategize like a chess grandmaster in a finance world full of checkmates.

    6. Starting Your Own Business: The Exciting Tax Maze

    Millennials may have been labeled as latte-sipping slackers, but they’re pulling an entrepreneurial Indiana Jones — dodging financial pitfalls while trying to find treasures! Yet, many gallivant into business without a clue about their entity structure. It’s like trying to dive into a pool without checking for water.

    Golden warns, “Operating as a sole proprietor may seem easy, but it’s like a tax trapdoor ready to open beneath your feet. Consider partnerships or S corporations if you want to dodge the high self-employment taxes — but be careful, or you might need to spend the next decade reorganizing.”

    7. Balancing Wealth with Risk Management

    Finally, they’re investing like it’s an Olympic sport! Stocks, ETFs, cryptocurrencies — millennials have their virtual hands in many financial pots. However, with great trading comes great tax responsibility. Frequent trading can hit your wallet with short-term capital gains taxed at ordinary income rates — a delightful surprise no one wants during tax season.

    “And don’t overlook cryptocurrency transactions,” Golden cautions. “Even if there’s no cash payment, the tax gods have their eyes on your crypto moves.” So, just like with your Tinder dates, make sure your investments and taxes keep up with one another; no one wants complications in either realm.

    The Grand Finale

    In the end, millennials are expertly navigating a financial funhouse, with tax concerns lurking around every corner. But armed with the right knowledge, they can avoid the pitfalls and come out on top — probably sporting a freshly squeezed green juice and a smile. So, remember, financial planning doesn’t have to feel like trying to keep five balls in the air; it can be mastered with a dash of strategy, a sprinkle of humor, and maybe a side of avocado toast.

    This article was provided by MoneyLion.com for information purposes only and should not be construed as definitive financial, legal, or tax advice. They don’t want to be responsible if you attempt to file taxes in a hot air balloon.

    CPA Distinct Identified issues Millennials Tax
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