I’m 57. I Retired at 55. Why Am I Still Afraid to Spend Money?

Retirement spending, early retirement, and the fear of spending money can feel strange after decades of saving. I retired at 55, and even with a solid plan, spending from the pile was harder than I expected. Before I retired, I thought the hard part was saving enough money. But after retiring early, I realized there’s another challenge people don’t talk about enough: learning how to actually use the money you spent decades building. In my first year of retirement, my fear around spending was probably an 8 out of 10. Now, in my second year, it’s closer to a 4. In this video, I share the 5 things that helped me lower that fear and feel more comfortable spending in retirement without being reckless. I talk about: - Why the fear of spending is often psychological, not mathematical - Why different buckets of money feel different emotionally - How a cash runway helps quiet market noise - Why flexible spending matters in retirement - How I separate spending into protection, joy, and noise - Why I don’t want to accidentally live like I’ve already run out of money The goal isn’t to die with the biggest portfolio possible. The goal is to use your money wisely while you still have the health, time, and freedom to enjoy it. 👇 Comment Below: Have you retired and have a fear of spending money? Or if you're not retired, have you thought of this? Let me know in the comments, I'd love to hear from you! ❤️ Like, Subscribe, and Share this video if you found the information in it helpful! ✅ Free resources available on my Patreon: All Roadmap tools, checklists, worksheets, downloads, and resources are now available for free! 👉 To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there. If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space. 💼 My Favorite Retirement Planning Tool, and that I mentioned in this video! 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! 🎧 Listen on the go: *Early Retirement Roadmap Podcast* Available wherever you get your podcasts! 🌐 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 video 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. #Retirement #RetirementPlanning #EarlyRetirement Chapters: 00:00 Why Am I Still Afraid to Spend? 01:16 Help #1 02:51 Help #2 04:07 Help #3 05:05 Help #4 06:39 Help #5 09:27 Legacy & Hidden Costs, 11:06 Patreon/Freebies