I Retired at 55: Here’s What I Wish I Did First

In this episode, I talk about the retirement strategy I wish I had seriously considered before leaving my career: easing into retirement instead of making it a hard stop.

For many people, retirement looks simple from the outside. One day you’re working, and the next day you’re done. But once you actually retire, you may realize work was providing more than just a paycheck. It may have also provided structure, routine, identity, social connection, and even the emotional permission to spend money.

That’s why a slower transition into retirement can make sense for some people — especially early retirees who need their money to last longer, may need to bridge the gap to Medicare, and may still be adjusting to life without a regular paycheck.

In this video, I’ll share why I think I could have handled my own retirement transition differently, how part-time work or consulting can soften the landing, why health insurance matters so much before Medicare, and how to think about retirement as more than just a financial decision.

Retirement isn’t just about asking, “Can I retire?” It’s also about asking, “How should I retire?”

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉 To get these free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap then click Join for Free, then click on the Tools collection. You can download any of them there.

💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap

Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you!

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

DISCLAIMER: This episode is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.

Tämä jakso on lisätty Podme-palveluun avoimen RSS-syötteen kautta eikä se ole Podmen omaa tuotantoa. Siksi jakso saattaa sisältää mainontaa.

Jaksot(65)

I’m 57 & Retired: What I Actually Do All Day

Wondering when you retire, what you're going to do all day? And is that fear of being bored one of things holding you back from retiring? I’m 57 and retired, and I’ll share what retirement actually fe...

22 Kesä 21min

I Retired at 55: 10 Money Traps I Refuse to Fall For

I retired at 55, and these are 10 things I refuse to waste money on. Retirement doesn’t mean you stop spending money. It means you get more honest about what the spending is actually for. In this epis...

15 Kesä 20min

Working Past 55? 6 Hidden Costs Most People Miss

Early retirement at 55 sounds like the dream — but after retiring early myself, I realized there are things I wish I had understood sooner about retirement planning, money, purpose, and life after wor...

8 Kesä 18min

I'm 57 & Retired: America Feels Too Expensive.

Early retirement, retirement planning, cost of living, healthcare, insurance, and retiring in America are all starting to feel different than many of us expected. I’m 57 and retired, and lately I’ve b...

25 Touko 14min

I’m 57 and Retired: 5 Things I Never Tell Anyone

Early retirement, retirement planning, and financial independence all require more than just money — they also require boundaries. I’m 57 and retired, and these are 5 things I never tell anyone. Some ...

18 Touko 18min

I Retired at 55: My 7 Layers to Avoid Running Out of Money

Running out of money in retirement is one of the biggest fears. I retired at 55, and in this episode, I share the 7 layers I use to protect my retirement plan. When I was preparing to retire early, I ...

11 Touko 30min

My Gen X Retirement Doesn’t Look Like a Boomer’s

Gen X retirement won’t look like Boomer retirement. Here’s why retirement planning is changing for Generation X, from Social Security to health insurance, 401(k)s, and early retirement. For many Baby ...

4 Touko 25min