Retirement Strategies Your Financial Advisor Should Be Discussing

9 October 2025

Retirement—it's that golden period of life where you finally have time to do all the things you've been putting off. Travel the world? Maybe. Golf every day? If your back allows it. Start a side business selling artisanal, hand-knitted socks? Hey, why not!

But before you sail off into the sunset, you need a solid financial plan in place. And guess what? Your financial advisor should be bringing up some key strategies to make sure you're covered. If they're not, it's time for a serious chat—or a new financial advisor.

So, grab a cup of coffee (or a stiff drink) and let’s break down the retirement strategies that must be part of the conversation.

1. How Much Money Do You Actually Need?

You’ve probably asked yourself, How much is enough? And your financial advisor should have a realistic answer, not just some vague “save as much as you can” speech.

A common rule of thumb is the 4% rule—you withdraw 4% of your savings per year, and theoretically, your money should last 30 years. But life isn’t a math equation, and things like inflation, medical expenses, and market crashes can throw a wrench in that plan.

Your advisor should be running different scenarios, factoring in everything—from worst-case to best-case—so you don’t end up greeting people at Walmart when you’re 85 just to pay the bills.

2. Social Security: When Should You Take It?

Social Security is like the world's slowest slot machine. The longer you wait, the bigger the payout. But should you wait?

- If you take Social Security at 62, you get less per month—but more years of payments.
- If you wait until full retirement age (typically 66-67), you get your full benefit.
- If you hold off until 70, you get an even bigger check every month.

Your financial advisor should be running the numbers to see what makes the most sense for your situation. If they're not, they're slacking.

3. Investments: Too Aggressive or Too Conservative?

Investing for retirement is a lot like Goldilocks' porridge—too hot (aggressive) and you might burn your savings in a market crash, too cold (conservative) and inflation will eat away at your money.

- Your 30s & 40s: Mostly stocks, high growth potential.
- Your 50s: Mix in more bonds and safer investments.
- Your 60s & beyond: Conservative but not too safe—you still need growth.

If your financial advisor hasn’t checked your portfolio in years, they might as well be looking at a weather report from 1998. It's outdated, it's useless, and it could be dangerous.

4. Healthcare Costs: Have You Planned for Them?

Fun fact: In retirement, you’re likely to spend more on healthcare than on travel or hobbies. (Not so fun, huh?)

Medicare kicks in at 65, but it doesn’t cover everything. You’ll probably need:
- Medigap or Medicare Advantage to cover out-of-pocket costs.
- Long-term care insurance—because nursing homes are insanely expensive.
- A health savings account (HSA) if you’re still working—it’s tax-free savings for medical expenses.

Your financial advisor should be talking about these things. If they just nod and say, “Don’t worry, Medicare will take care of it,” you might want to worry a lot.

5. Taxes in Retirement: Because the IRS Doesn’t Retire

You thought taxes would get easier in retirement? Think again.

Your financial advisor should have a tax strategy in place, because:
- Social Security can be taxed (yep, they take some of it back).
- 401(k) and traditional IRA withdrawals are fully taxable.
- Required Minimum Distributions (RMDs) kick in at 73—and if you forget to take them, the penalty is massive.

Some strategies to consider:
- Roth conversions (pay the tax now, withdraw tax-free later).
- Municipal bonds (tax-free interest income).
- Withdrawing from different accounts strategically to minimize tax impact.

6. Passive Income: Because Who Doesn’t Love Free Money?

Retirement doesn’t mean you stop making money. It means you start making it passively—aka, while sitting on your couch.

Some great passive income streams:
- Dividend stocks (companies that pay you just for owning shares).
- Real estate rentals (tenants pay, you collect).
- Annuities (turn a lump sum into guaranteed income).

Your financial advisor should be discussing passive income options now, so you’re not scrambling later.

7. Estate Planning: What Happens When You’re Gone?

Look, no one wants to talk about what happens after they kick the bucket. But if you don’t plan, the government decides where your money goes. Spoiler: That’s not ideal.

A proper estate plan includes:
- A will (because you should say who gets what, not a judge).
- A trust (great for avoiding probate and reducing taxes).
- Beneficiary updates (your ex-wife shouldn’t still be on your life insurance).
- Powers of attorney (someone needs to make decisions if you can’t).

If your financial advisor isn't talking about estate planning, they’re ignoring a huge piece of the puzzle.

8. What Happens if a Market Crash Hits?

Markets go up, markets go down. But how you react determines if you retire stress-free or end up back at work.

Your advisor should have a strategy in place for downturns, like:
- A cash reserve (so you don’t sell investments at the worst time).
- A diversified portfolio (so all your eggs aren’t in one basket).
- A stress test for your finances (running worst-case scenarios).

If their best advice is "Just ride it out," that’s not a strategy—it’s hope. And hope is not a financial plan.

Final Thoughts: Is Your Advisor Covering All This?

Retirement planning isn’t just about saving money—it’s about using it wisely so you don’t end up broke, stressed, or moving in with your kids (spoiler: they probably don’t want that).

A good financial advisor should be discussing all these strategies. If they’re not, it's time to ask some tough questions—or find someone who will talk about them.

Because retirement should be about freedom, not financial fear. And honestly, you deserve that beach vacation (or that artisanal sock business—no judgment).