Jason Fletcher, CFP

Call Directions Website Contact the business

Jason Fletcher, CFP Provide Financial Education & Ideas for people.

A reminder for anyone on Medicare (or with a parent who is) — tomorrow kicks off Medicare's open enrollment window, and ...
10/14/2026

A reminder for anyone on Medicare (or with a parent who is) — tomorrow kicks off Medicare's open enrollment window, and it runs through early December.

This is genuinely one of the only chances each year to switch plans if your current one isn't serving you well anymore. Costs and coverage shift every year, so it's worth a real look, not just auto-renewing without checking.

Happy to help you or a family member sort through the options — just send me CHECK-IN.

As promised, here's your Open Enrollment Tip of the day: HSA and FSA are not the same thing, and mixing up the strategy ...
10/12/2026

As promised, here's your Open Enrollment Tip of the day: HSA and FSA are not the same thing, and mixing up the strategy can cost you.

🟡 HSA — great tax tool, money rolls over, no rush to spend it

🔴 FSA — mostly "use it or lose it," so don't overestimate just to be safe

Five minutes of thought NOW can make a real difference by December...Just sayin'. 😉

Not sure which fits your situation? It can be a lot for anyone, but don't fret! Send me CHECK-IN and let's figure it out together.

Heads up — open enrollment season is almost here, and I don't want anyone clicking through it at 9pm without a second th...
10/12/2026

Heads up — open enrollment season is almost here, and I don't want anyone clicking through it at 9pm without a second thought.

Over the next few days I'll be sharing a few things worth actually looking at this year before you finalize anything.

First tip: don't treat this as a standalone HR task. Your elections this week affect your taxes and cash flow for the whole next year.

Want a head start on the conversation? Send me CHECK-IN anytime.

Open enrollment season is here, and I already know what's happening in a lot of households right now — someone's clickin...
10/07/2026

Open enrollment season is here, and I already know what's happening in a lot of households right now — someone's clicking through a benefits portal at 9pm, just trying to get it done before the deadline.

Here's what I want people to know going in: open enrollment isn't just an HR formality. It's one of the few times a year your choices directly shape your taxes, your cash flow, and your long-term plan — all in one sitting.

A few things worth a real look this season:

→ Your HSA contribution — one of the most underused tax tools out there

→ Your FSA elections — most of those dollars don't roll over, so overestimating hands money back at year-end

→ Life insurance and disability coverage through work, especially if your situation has changed

→ Medicare coverage, if that applies to you — plans and costs shift every year

None of these decisions happen in a vacuum. Your HSA strategy connects to your retirement plan. Your insurance elections connect to your emergency cushion. That's the piece that gets missed when open enrollment gets treated as a solo HR task instead of part of the bigger financial picture.

This is exactly the kind of thing worth a second set of eyes on before you click submit.

If you want a second opinion before you finalize your elections this year, send me CHECK-IN.

Every year around this time, I get the same nervous phone call: "Jason, did you see what the market did today?"Here's th...
10/07/2026

Every year around this time, I get the same nervous phone call: "Jason, did you see what the market did today?"

Here's the truth — September has historically been a rocky month for stocks. Nobody has a clean explanation why. But here's what I do know after 25+ years of doing this: it's not the dip that hurts people. It's the panic.

A quick gut-check worth doing this month:

✅ Make sure your emergency savings are solid

✅ Double-check your portfolio still matches your actual risk comfort

✅ Remind yourself — a rough week in the market isn't the same as a change in your real goals

Staying calm and staying invested is still one of the smartest moves you can make.
Want a second set of eyes on your plan before Q4 hits?

Send me a message with CHECK-IN — happy to talk it through, no pressure.

Happy Labor Day! 🇺🇸Today is a good day to pause and recognize the people whose hard work keeps our families, businesses,...
09/07/2026

Happy Labor Day! 🇺🇸

Today is a good day to pause and recognize the people whose hard work keeps our families, businesses, communities, and economy moving forward.

Whether you’re building a business, serving customers, raising a family, working with your hands, or simply doing your best to create a better future — your work matters.

When should you take Social Security?62? 67? 70?You'll find plenty of people online who will confidently tell you there'...
08/30/2026

When should you take Social Security?

62? 67? 70?

You'll find plenty of people online who will confidently tell you there's one "right" answer.

There isn't.

Your best decision depends on your individual situation. Things like:

• Your health
• Your spouse
• Other retirement income
• Your savings
• Your spending needs
• Your tax situation
• How long you expect to live

The important thing is not simply figuring out when you can claim.

It's figuring out how Social Security fits into the rest of your retirement income.
That's a very different question.

If you're nearing retirement, it's worth looking at the whole picture before making the decision.

Do you really need a financial advisor once you're retired?Maybe. Maybe not.If your financial life is simple and you're ...
08/27/2026

Do you really need a financial advisor once you're retired?

Maybe. Maybe not.

If your financial life is simple and you're comfortable managing everything yourself, you may not need one.
But retirement can get complicated quickly.

You may have:

• Social Security
• A pension
• Several retirement accounts
• Investments outside retirement
accounts
• Required minimum distributions
• Medicare considerations
• Charitable giving goals
• An estate plan
• A spouse who depends on your income

The bigger question isn't: "What investment should I buy?"

It's: "How do all of these pieces fit together?"

A good retirement plan should help you understand where your income will come from, how much you can comfortably spend, how much risk you're taking and how today's decisions could affect your future.

If you're retired—or getting close—what financial question keeps you up at night?

If you're a high earner, August may be more important than December.Why?Because December is when many financial decision...
08/23/2026

If you're a high earner, August may be more important than December.

Why?

Because December is when many financial decisions become urgent.

August is when you still have time to make them strategically.

For high-income professionals, entrepreneurs and business owners, a midyear review can uncover opportunities around:

• Retirement savings
• Investment allocation
• Portfolio diversification
• Business planning
• Cash flow
• Tax-efficient investing
• Roth strategies
• Estate planning
• Risk management

The question isn't:

"What can I do to reduce my taxes?"

The better question is:

"Are all of my financial decisions working together?"

That's the difference between reacting to your financial life and actually planning for it.

I wrote a new guide:

The High-Earner's Midyear Financial Checkup: 8 Questions to Ask Before Year-End

Read it here → https://dfc-wealth.com/jasons-blog-1?blog=y

Your tax return is a rearview mirror.It tells you where you've been.But high earners need a windshield.If you're a lawye...
08/12/2026

Your tax return is a rearview mirror.

It tells you where you've been.

But high earners need a windshield.

If you're a lawyer, entrepreneur, executive or business owner, your financial picture can change dramatically in just six months.

Income changes.

Investments move.

Businesses grow.

Bonuses arrive.

Equity gets complicated.

Retirement opportunities change.

And suddenly, the financial plan you created in January may no longer reflect your reality.

That's why August is a good time for a midyear financial checkup.

Not to obsess over taxes.

To ask bigger questions:

→ Is my retirement strategy keeping pace with my income?

→ Is my investment portfolio still appropriately diversified?

→ Am I taking too much risk in one area?

→ Is my business strategy connected to my personal wealth strategy?

→ Are my tax, investment and retirement decisions working together?

→ What needs to change before December?

Your financial plan shouldn't be something you look at once a year.

It should evolve as your financial life evolves.

I put together an 8-question Midyear Financial Checkup specifically for high earners, entrepreneurs and successful professionals.

➡️ https://dfc-wealth.com/jasons-blog-1?blog=y

Address

2217 Crystal Springs Avenue Ste 114
Roanoke, VA
24014

Telephone

+12404473377

Website

Alerts

Be the first to know and let us send you an email when Jason Fletcher, CFP posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Jason Fletcher, CFP:

Shortcuts

Share

Category