4 Ways Investing for Retirement is a lot like Fantasy Football

It’s football season! Which means (wait for it)… Fantasy Football!! 

It’s football season—and you know what that means: fantasy football is back in full swing! Whether you're an ESPN, Yahoo, or Sleeper guy, the fantasy world and investment world share more in common than you'd think.

🧠 1. Don’t Gamble with Your Top Pick

Just like you wouldn’t use your first-round pick on a kicker, you shouldn’t put your top dollars into a speculative investment. Instead, anchor your portfolio with solid, time-tested foundations—like broad-based index funds such as the S&P 500, which has historically returned around 10% annually. Want to chase alpha? Fine—but keep it small and discretionary. There are no redrafts for retirement.

🎯 2. Balance Your Roster—and Your Portfolio

Fantasy strategies vary: “zero RB,” “Robust WR depth,” "Hero RB," two-QB streams—yet balance often prevails. Similarly, avoid overconcentration. Blend large-cap, mid-cap, small-cap, international, and maybe bonds depending on your situation. Bonds may not win championships, but they help avoid catastrophic losses—like a dependable backup QB.

🔁 3. One Bad Week Doesn’t Signal a Bust

A star QB (or WR) doesn’t lose prime status after one poor game. Likewise, don’t drop a promising fund just because it lags a benchmark briefly. Compare like to like—small cap to small cap—not your Small Cap Fund to the mighty S&P 500. Let underperformers breathe unless consistent underperformance shows a deeper flaw.

🏈 4. Chasing Hot Picks Is a Recipe for Disaster

That waiver-wire breakout star might flame out against tougher competition—and the same goes for investment trends. Outperformance one year doesn’t guarantee another. A consistent, disciplined approach typically beats chasing "what’s hot right now." See asset class returns below.

(Bonus) Get the Whole Team, Not Just the Star

Want Patrick Mahomes on your roster? He'll have some great weeks, and he might have some not-so-great weeks. Rather than betting on Mahomes alone, own a slice of all his teammates (who doesn't want some Travis Kelce in the mix?!?). ETFs and mutual funds do exactly this—providing diversification and reducing risk from any one player (or company) going down or underperforming.

🆕 2025 Updates

• More fantasy platforms: ESPN still has overall popularity, but league dynamics vary—Yahoo, Sleeper, CBS, and even NFL.com are thriving.

• Fantasy experts: Without Matthew Berry at ESPN, top voices now include Field Yates, Stephania Bell, and Mike Clay, but analysts on NBC’s Fantasy Football Happy Hour, featuring Matthew Berry, Jay Croucher, and Connor Rogers is the Hill-Top go-to for daily fantasy advice and entertainment.

• Investing platforms: Charles Schwab, Fidelity, Vanguard, E-Trade and robo-advisors like Wealthfront or Betterment are go-to options.

• New asset classes: While bitcoin once sparked speculation (and still does by many), today's focus leans towards diversification with crypto (bitcoin)—still speculative, but with more widespread adoption and accessibility (spot bitcoin ETFs).

• Fee structures: Retainer-based financial planning continues to grow, appealing to investors looking for objective financial advice.

✍️ Final Takeaway

Fantasy football and retirement investing both hinge on strategy, diversification, and discipline—not hype. Build around proven core assets, allocate for upside, ignore short-term noise, and don’t chase flash-in-the-pan performers.

Need some draft-day coaching—for your finances?

If you’d like one-on-one guidance in building your financial roster, I offer complimentary 30-minute introductory calls. Let's draft your plan together!

Kyle Hill, CFP®, is a CERTIFIED FINANCIAL PLANNER™ professional located in Kansas City, MO, serving clients across the nation. He is the owner, founder, and financial planner of Hill-Top Financial Planning, LLC, an independent, Fee-Only registered investment advisor in Missouri and Kansas. The firm offers comprehensive financial planning and investment management services to professionals and families. Kyle assists clients in creating personalized financial plans to provide clarity in their financial situations, enabling them to build wealth and achieve financial independence. He addresses a wide range of personal financial topics, including budgeting, cash flow planning, investing, retirement savings, college savings, insurance planning, tax planning, and more. Hill-Top Financial Planning, LLC operates as a fiduciary and does not earn any commissions.