Start Building Your Someday

We all grew up with someone else's definition of success. Corner office, golden watch, retirement at 65... sound familiar?

Here's the thing: You get to write your own rules now.

Five years ago, we were stuck in the "someday" trap. Someday we'd have more time. Someday we'd travel more. Someday we'd build a life that actually fit us. Then we got serious about what we really wanted: more time together, work we could do from anywhere, and the freedom to explore. 

We started researching remote work, looking at our expenses differently, and opening our minds to possibilities we'd never considered before. That's when Portugal appeared on our radar – and suddenly "someday" had a clear path forward. Today, we're living a life we couldn't even have imagined back then.

But your "someday" might look completely different:

• Maybe it's turning your vintage camera collection into an online shop

• Perhaps it's teaching English online while RVing across national parks

• Or it could be consulting 15 hours a week so you can spend more time with grandkids

The new success formula is simple:

• Choose work that energizes you

• Design your days around your natural rhythm

• Live where your money goes further

• Keep your skills sharp but your schedule flexible

Small steps get you there:

1. Start with your non-negotiables:

   • How many hours do you want to work?

   • Where do you feel most alive?

   • What monthly income do you need?

2. Test drive your dream:

   • Try a month of remote work

   • Visit potential new homes

   • Start a side project

Remember this: The "right" path is the one that makes you excited to start each day.

You've spent decades building skills, judgment, and wisdom. Now it's time to use them to craft a life that fits YOU perfectly.

Would love to hear: What's your version of "someday"? Hit reply and let us know what freedom looks like for you.

Happy adventuring,
Matt and Dawn

SPONSORED CONTENT

EXPAT LIFE

Moving to Portugal Online Course is Live!

We’ve officially opened up our Moving to Portugal Course to the public! 🎉

If you’ve been wondering how to make this move without the overwhelm, we’ve got you covered.

The course walks you through every step of the process—from figuring out if Portugal is right for you, to visas, housing, healthcare, and building a life here.

This isn’t just a list of to-dos. It’s all the practical advice we wish we’d had (including tips to save time, money, and headaches).

If Portugal is calling your name, check it out here → Moving to Portugal Course

FLEXIBLE INCOME

Build Flexible Income Streams in 2025

If you’ve been thinking about starting a side hustle or building online income this year, you’re not alone.

The question is: Where do you start?

Our Over 50 Online Income Handbook is a great place to begin. It breaks down 12 beginner-friendly ways to earn your first $1,000 online, along with 90-day action plans to help you get there.

And here’s the thing—you don’t need to be tech-savvy, have a big social media following, or reinvent the wheel. The key is starting small and building from there.

Grab your copy and start planning your first win: Over 50 Online Income Handbook

TRAVEL AND ADVENTURE

Coimbra, Portugal is Having a Moment - and It’s Long Overdue

Coimbra, Portugal has made the New York Times list of 52 Places to Go in 2025, and we could not be more thrilled! 

Coimbra is the unsung hero of Portugal’s big cities with so much to explore. Located in Central Portugal, Coimbra is Portugal’s third largest city and home to one of the oldest universities in Europe (established 1290). 

The city is also a foodie’s paradise - some of our favorite meals in Portugal have been in Coimbra. 

Whether you’re planning a trip to Portugal or just looking for some travel inspiration, the New York Times list is filled with ideas for your next adventure. 

See the list →