u/Admirable_Street2372

Hi all! I'm a 31F, high income earner, looking for a sanity check on Roth IRA + overall financial strategy

Background:

• Age: 31
• Income: ~$325k–$350k (W-2, stable for next few years)
• Homeowner
• Goal: Financial independence / optional retirement by ~50
• 12 months emergency already saved in a HYSA

Debt:

• ~$221k federal student loans @ 5.88%
• Plan: aggressive payoff (target ~5 years, possibly sooner by throwing bonuses/lump sums at it)
• Likely using a standard 10-year structure but paying ahead

Retirement accounts:

• Maxing 401(k) (have been maximizing for almost 2 years now in an ETF fund!)
• Doing backdoor Roth IRA annually

Current Roth IRA allocation (~$15k total):

• ~25% FXAIX (S&P 500 index)
• ~20% ITOT (total US market)
• ~12% IYY (Dow Jones ETF)
• ~9% VOO (S&P 500 again)
• ~18% HIMS (individual stock — currently down ~40%)
• ~17% cash (about to deploy another $7,500 contribution)

Questions / where I’d love feedback:

1. Am I overcomplicating my Roth? I realize I have a lot of overlap (FXAIX, VOO, ITOT, IYY all essentially US large-cap exposure) and open to changing
2. Is holding an individual stock (~18%) in a Roth a bad move, especially given the loss? Hold vs cut?
3. Would you simplify this to something like total market + international?
4. Given my income and goals, should I be prioritizing anything differently between:
   • Tax-advantaged investing
   • Brokerage investing
   • Student loan payoff
5. Anything else I’m missing for a FIRE-by-50 trajectory at my income level?

I feel like I’m doing a lot “right” but maybe not optimizing. Open to any critiques or suggestions, especially from those further along. Thank you all!

Hi all! I'm a 31F, high income earner, looking for a sanity check on Roth IRA + overall financial strategy

Background:

• Age: 31
• Income: ~$325k–$350k (W-2, stable for next few years)
• Homeowner
• Goal: Financial independence / optional retirement by ~50
• 12 months saved in a HYSA

Debt:

• ~$221k federal student loans @ 5.88%
• Plan: aggressive payoff (target ~5 years, possibly sooner by throwing bonuses/lump sums at it)
• Likely using a standard 10-year structure but paying ahead

Retirement accounts:

• Maxing 401(k) (have been maximizing for almost 2 years now in an ETF fund!)
• Doing backdoor Roth IRA annually

Current Roth IRA allocation (~$15k total):

• ~25% FXAIX (S&P 500 index)
• ~20% ITOT (total US market)
• ~12% IYY (Dow Jones ETF)
• ~9% VOO (S&P 500 again)
• ~18% HIMS (individual stock — currently down ~40%)
• ~17% cash (about to deploy another $7,500 contribution)

Questions / where I’d love feedback:

1. Am I overcomplicating my Roth? I realize I have a lot of overlap (FXAIX, VOO, ITOT, IYY all essentially US large-cap exposure) and open to changing
2. Is holding an individual stock (~18%) in a Roth a bad move, especially given the loss? Hold vs cut?
3. Would you simplify this to something like total market + international?
4. Given my income and goals, should I be prioritizing anything differently between:
   • Tax-advantaged investing
   • Brokerage investing
   • Student loan payoff
5. Anything else I’m missing for a FIRE-by-50 trajectory at my income level?

I feel like I’m doing a lot “right” but maybe not optimizing. Open to any critiques or suggestions, especially from those further along. Thank you all!