Written by Hi, I’m Dre Griggs with Obsidian Wisdom, and if you just turned 50, this one’s for you. Because let’s be real… hitting 50 can be a wake-up call. Suddenly you’re thinking, “Do I have enough saved?” “Can I retire when I planned?” “What about healthcare or a market crash?”
The good news? You’re not too late. In fact, this is the perfect time to tighten up your plan. Let’s walk through five smart moves I use with my clients to help them reassess retirement with confidence. Even after 50.
1. Know Where You’re At (So You Can Know Where You’re Going)
You can’t create a solid plan without first knowing your starting point. That means looking at:
- Your income and how much of it you’re saving.
- Your current retirement savings and how you’ll turn that into income.
There are three main ways to build retirement income:
- Real estate (rental income, leverage opportunities)
- Stock market (dividends, growth, diversified income streams)
- Personal business (you can generate revenue without needing as much upfront capital)
Most people don’t realize this, but where you invest affects how much you’ll need. If you’re earning rental income or own a business, your required nest egg may be smaller than if you rely only on the market.
And speaking of the market… the top 10% of wealth controls nearly 90% of it. That’s not to scare you; it’s to remind you that it’s a powerful place to grow wealth when used wisely.
2. Create a Debt Elimination Plan That Makes Sense
Here’s where most people get stuck: debt. But I’m telling you — if we clean this up, you might not have to wait 10 more years to retire. Maybe it’s 10 months.
Start by asking:
- What percentage of your income is going to debt?
- Can we reduce that so your retirement income need is lower?
Sometimes, it’s about paying off high-interest debt. Other times, it’s about quick wins. Paying off smaller balances for the psychological boost. Either way, the goal is a sustainable plan that frees up income.
Pro tip: If you’ve got a pension and no debt, you might already have enough to retire now.
3. Realign Your Retirement Goals and Lifestyle Vision
Let’s talk dreams.
Most folks over 50 haven’t really defined what retirement looks like for them. They just know they don’t want to keep doing what they’re doing. But if you don’t know what your dream life costs, how can you plan for it?
- Want to travel? How often?
- Volunteer? With who?
- Visit grandkids? Live near them?
You might find your dream life costs less than your current lifestyle — and that’s a big opportunity. But if it costs more, we need a strategy to get you there.
4. Reassess Your Investment Allocation
At 50+, you’ve got to balance growth with safety.
The stock market can drop 20–30%, sometimes even more. If retirement is around the corner, that’s a big risk. So now’s the time to review your asset allocation.
I use a three-bucket strategy with my clients:
- Bucket 1 – Cash or cash equivalents (1–2 years of expenses)
- Bucket 2 – Income-producing investments (bonds, annuities, etc.)
- Bucket 3 – Growth investments (stocks, real estate, business)
This setup gives you flexibility. If the market crashes, your cash covers you. Your income bucket buys you time. And your growth investments recover.
Don’t forget your catch-up contributions:
- 401(k): Extra $7,500 if you’re 50+
- IRA: Extra $1,000
- HSA: Extra $1,000 if you’re 55+
More money in tax-advantaged accounts = stronger retirement.
5. Update Your Income Plan
A strong income plan answers this: “Where is my retirement paycheck coming from?”
Social Security? Pension? Investments? Rental income?
And it adapts when life changes.
- Got divorced? Income plan changes.
- Lost a spouse? Changes again.
- Downsizing? You guessed it… new plan.
We also want to ask: Should we do a Roth conversion? If you’re over 50, this could be a powerful way to reduce taxes later by paying a little now.
This is the time to:
- Calculate your income needs
- Identify any gaps
- Decide if you want to work longer, spend less, or contribute more
Bonus: Plan for Healthcare Now (Not Later)
Most retirement plans miss this completely. But healthcare can eat up $200K–$400K in retirement — and that’s before long-term care.
Here’s the deal:
- 70% of folks 65+ will need long-term care
- It costs ~$50–$60K per year
- It often lasts 2–3 years
Even if insurance isn’t in your budget, we can get creative:
- Budget a set-aside fund
- Bring in part-time care
- Use HSA savings for medical expenses (triple tax benefit!)
And yes… if you’re married, consider a plan that protects your spouse too.
Lifestyle Planning: Your Purpose & Pleasure
Retirement isn’t just about money. It’s about what you do with your time.
One of my favorite books, Happiness by Design, talks about how happiness comes from balancing purpose and pleasure.
For example:
- Purpose = volunteering, mentoring, helping your family
- Pleasure = travel, concerts, hobbies
- Both = kickball with your grandkids (yes, really!)
A lot of folks retire without a clear vision and end up bored or unhappy. Let’s not do that. List your goals:
- Short-term (1 year)
- Mid-term (3–5 years)
- Long-term (5+ years)
And every time you check one off? Add a new one. Your plan should grow with you.
Final Thoughts
Planning for retirement after 50 is all about wisdom over worry. You’re not too late, but you do need to take action.
If you want help with your personalized retirement plan, come join me for Worry-Free Wednesdays… my live session where we dive deeper into strategies like these and answer your questions.
Click here to register for the next Worry-Free Wednesday
Let’s take the fear out of retirement planning and replace it with confidence.
Image from: Freepik.com