profile

Jesse Cramer

So, You're Retiring? Answering Common Questions from Soon-to-Be Retirees ❓

Published 13 days ago • 1 min read

Good morning!

Today's email includes:

-- some data and theory about US stocks vs. international stocks

-- a good lesson about withholding taxes from Roth conversions

--a podcast episode about the final glide into retirement

--other great content about life lessons, cybersecurity, and market indicators

...and more...

...and more...

Will US Stocks Continue to Outperform International Stocks?

US stocks have outperformed international stocks by a surprising margin over the past 55 years.

So - is it worth owning international stocks on a go-forward basis?

After all - why own underperformers?

Well...there's more here than meets the eye.

If "the market" is allocating money to international stocks, but you're not, are you making some sort of active bet?

Read on...

Do *Not* Withhold Taxes from Your Roth Conversions

A reader wrote in to me last week explaining his DIY retirement plan.

His plan involved Roth conversions. No problem so far.

Roth conversions create taxes. Indeed, unavoidable.

And his plan was to pay those taxes via withholding dollars from the Roth conversion.

Hold up!

Read more below to learn what the problem is.

Sometimes even the "simple" actions in our retirement can inadvertently do damage.

Gliding into Retirement

The approach into retirement raises dozens of questions.

Some questions about numbers

Many questions about feelings.

Listeners like you have many questions about the transition into retirement.

Today's "Ask Me Anything" episode is dedicated to your retirement transition questions.

Tune into Episode 147 - So, You're Retiring? Answering Common Questions from Soon-to-Be Retirees.

The Top 3...

I enjoyed this content recently. I hope you do too.

​10 Truths from Doc G​

Jordan Grumet published 10 lessons from his 53 years on Earth. My favorite comes from #3:

"I can promise you this: people at the end of their lives do not regret their failures. They regret the deeply important things they never had the courage to try. True contentment comes from intentionally putting yourself in the arena."

​Cybersecurity​

Fritz from The Retirement Manifesto spent ~1 hour to improve his cybersecurity scorecard from "Good" to "Excellent."

I'm thankful he shared his moves step-by-step.

​Indicators.​

Market indicators work...until they don't.

One of the challenges of complex adaptive systems (like investment markets) is that certain signals might appear very strong.

But if everyone is aware of them, then they're worthless!

I Help People Retire (Even) Better

I'm a Partner at a fee-only fiduciary retirement planning firm.

We work with clients all over the USA.

If you know someone who needs help, visit PlanWithJesse.com and let's start a conversation.

Until Next Week...

Thank you for reading, listening, and writing back.

People like you send me questions every day.

I'd love to hear from you. ​​

All the best,

Jesse Cramer

Jesse Cramer

Smart ideas about money and retirement.

Retirement is a different game. You’ve spent decades building wealth. Now comes the harder part - turning it into a paycheck that lasts. I’m Jesse Cramer. I help DIY investors turn their savings into a clear, cohesive retirement plan. Join 4000+ weekly readers and 20,000+ podcast listeners.

Read more from Jesse Cramer
top view photography of broken ceramic plate

Good morning! If you're in Southern California, I have a quick question for you below. Otherwise, on with the show! Today's email includes: --thoughts on longevity --questions you should ask about your financial plan --great content about Bogleheads, health & wealth, and a "wizard" who lost all his investors' money ...and more.. Are You in SoCal? Do you live near... Huntington Beach? Palm Springs? San Diego? I'm speaking at back-to-back conferences the week of September 14-18. FutureProof in...

5 days ago • 2 min read
shot by @ammaramir

Good morning! Today's email includes: --The concept of "full price" ⌛ --The hidden 90% of investment account statements 🫣 --Healthcare in retirement, denominators, and giving it away... 🩺 ...and more... The Importance of Full Price We all notice the sticker price. That bicycle costs $400. That's the sticker price. And some of us think about opportunity cost. You spend money now, but you could have more money later. A bird in hand vs. two in the bush. That's opportunity cost. If you invested...

20 days ago • 1 min read

Good morning! Scenes of summer here in Upstate NY. Our elder daughter loves to swim. It's hard to go wrong with a pool + a grilled cheese sandwich. Today's email includes: 🧸 Some thoughts before the (next) bear market. 🫙 What you might be missing on your investment account statements. 👀 Some interesting news about what the IRS is paying attention to ...and more= Jesse on Some Other Podcasts... Many thanks to Paul Lambert and Chris Hill and Joe Saul-Sehy for inviting me on their excellent...

27 days ago • 1 min read