#17: Let’s Talk Lifestyle Businesses

newsletter Nov 05, 2023

Thanks for all the messages. The feedback has been overwhelming for me. Thank you!

And relative to your journeys…

I know it’s hard to redesign or simplify day-to-day. Keep going. Keep removing blockers to time, financial, and geographic freedom. Keep building relationships, helping people while they help you. Need help getting over blockers? Refer to Newsletter 9. Don’t give up on dreams, ever.

I’m having my own challenges, missed opportunities, and relationships. Doesn’t matter. Respect your process and the people in it. In the end, happiness and lifestyle are worth the effort. Yes, you can.


Over the past few weeks, I’ve visited the following kinds of businesses:

  • Small Coffee Shop
  • Organic Farm
  • Property Management Company
  • Art Gallery & Working Studio
  • Boutique Bed & Breakfast/Hotel (see video)

My search has mainly been in the Eastern Mediterranean because that’s where the next phase of life is on my end. They’re not huge money-makers, nor is that the point. They are Lifestyle Businesses, a way to plug into the community, connect to people, and create lifestyle.

What’s a Lifestyle Business? A lifestyle business focuses on the owner's preferred way of living, rather than the relentless pursuit of profit and growth. Think prioritizing personal fulfillment and a craft life you want while earning a living rather than the ‘world domination of business’ pushed by social media.

Think connecting with the local community meaningfully, the person everyone knows.

My friend Nichola is one of those people. I visited him for the 4th time recently, and he and I had the lifestyle conversation again. He’s mentored me on the topic.

He and his wife run a 5-bedroom boutique hotel and coffee shop specifically started to support how they wanted to live, not to necessarily make millions of dollars. What they wanted was to be central to the community, earn friendships, and be available for family – all my very goals.

What struck me about his business was how the entire family is involved, how his young daughter is always around, and everybody knows her. They seem so happy to be providing a service to the community.

They took their hard-earned and saved money and created a unique lifestyle for themselves.

When someone asks you what you do for a living, what if you answered as follows…

“Our lifestyle business is a boutique bookstore and café located in a trendy neighborhood. The business is a family endeavor, and it's a labor of love that reflects shared passion for literature, art, and good food. The bookstore is haven for bookworms and art enthusiasts, and the café offers artisanal drinks, pastries, and light meals.

Mornings are filled with the aroma of freshly brewed coffee and chatter of our regular customers. As a family, we curate the bookstore's collection, host book clubs, and organize art exhibitions, creating a welcoming and intellectually stimulating space for the community.

Financially the business generally supports everything we need, but any temporary struggle is worth it because we get to do what we love each day – work with each other and build community in the city.”


Especially later in life and for those wanting to live in unique environments (by the sea, in the mountains or country, boutique cities), or those simply wanting to get away from traditional rat race employment, lifestyle businesses are on the rise.

They don’t necessarily have to be brick and mortar. It could be a virtual business like a consulting practice; digital marketing services including like social media writing & editing. Or maybe blogging services, essentially businesses related to individual interests. But with the virtual world you miss the in-person community aspect, which I see as most important.

People make life. Community and social interaction are big parts of happiness.

The cool thing is more and more people are choosing to venture down this path. And it’s giving people “purpose” at their regular jobs…

“…I’m going to work another 4 years and save money to open my lifestyle business”.


I regularly think about the fact that we’re encouraged to save/invest for retirement. What if we had been encouraged to work traditional employment for 5-15 years and save money to invest in a lifestyle business for a more, fulfilling existence later?

Just a thought from my perspective.

I’m not saying lifestyle businesses make sense for everyone. What I am saying is they’re a great tool to develop living the way you want, where you want.

Obviously, the choice depends on your personal preferences, financial and family goals, risk tolerance, and career aspirations. But it is a choice, nonetheless. And that’s what I wanted to bring to your attention.

Have a great week!

Try Life On