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snowbird entrepreneur beach

A few weeks ago, I posted a question in the Slow FI Enthusiasts Facebook group asking people to “raise their hand” if they had designed a life they didn’t want to retire from

I want to learn as much as possible from people who have done this because this is the kind of life I want to build for myself.  

Kari was one of these people! About 10 years ago, Kari told me that she came across the term “lifestyle entrepreneurship.” It referred to building a business that allows for maximum flexibility to live the life you want.  

Kari’s dream was to become location independent so that she could travel south (from her home in Indiana) as a “snowbird” for the winters.  

It took time to put the building blocks in place. Excitingly, Kari quit her job in 2020 to build her lifestyle business and took her first “snowbird” excursion in February of 2021.  

Let’s get into the interview so Kari can share more about how she made this dream a reality.  

1. Tell me a little bit about you. 

I’m Kari. I am a kayaking, hiking, bean-counting, always-learning, debt-free, 47-year-old DINK from Southern Indiana. 

woman beach

My career background over the last 25 years includes program management for nonprofit organizations, business consulting, and being self-employed doing screen printing and graphic design. Now, I run a business called the Penny Tracker that provides bookkeeping services, QuickBooks software training, and organizational workflow consulting for small businesses. I provide business services virtually, which allows me to work from anywhere. 

2. What deliberate decision have you made to slow down and improve your life? Why did you decide to make this decision?

In the summer of 2020, I quit my management role at a state agency to start my own business. And, I started a business that would provide me with the lifestyle I wanted, which included:

  • Flexible work time 
  • Consistent monthly revenue with opportunities to dial-up or down income as I choose 
  • Ability to work from anywhere, so that I could head south for the winter 

This lifestyle change has been many years in the making and it was inspired by my mom, who passed away when I was 24 from a short, but brutal, battle with breast cancer. She was 59. My mom never got to experience retirement. She never took that trip to Hawaii she and my dad had talked about for years. She impacted so many lives while she was on the planet, but she didn’t get to create so many of the memories she dreamed about.  

Those realizations settled deep in my soul and made me look at life differently than most people. While I would love to have my mom back, I’m grateful that my perspective was shaped in my early 20s to pursue a life of meaning and memories.  

During my mid-30s, I came across the idea of “lifestyle entrepreneurship” and the concept of living a life you don’t need a vacation from. I’ve never held high-paying jobs where I could buckle down for a few years to reach financial independence. I also realized that I enjoy working as long as I have flexibility and control of my day.  

At that point, I decided I wanted to be able to “snowbird” in the winter (like my retired dad), but I wanted to do it long before I was 65 or 70. I love Southern Indiana most of the year, but I’m not a fan of weeks of gray skies, cold temperatures, snow, and ice.  

It took me a decade of additional work experience, brainstorming, and personal development to get all of the pieces in place to fully pursue my dream of building a lifestyle business. Now, I run a business that allows me to generate a full-time income in part-time hours. And, I can do my work from anywhere.  

beach sunset sand

In February of 2021, I did my first “snowbird” excursion. I spent the entire month living in a condo on the beach in Gulf Shores, Alabama. In 2022, I spent five weeks there! 

My husband also owns his own business, but he’s not yet in a position where he could leave it for 4-5 weeks. So, he joined me for a couple of weeks and then returned home. He’s now focusing on adapting his business model so that we can both head south for at least 6 weeks next year together. 

3. How has the decision to start a lifestyle business impacted your quality of life? 

I’m almost embarrassed to describe how much this path has improved my life. Now, I wake up without an alarm. I have minimal stress. I have the freedom to choose what almost every day looks like. I don’t have financial or relationship worries.  

Now that the business has a stable footing, I have time and mental energy to focus on my personal health habits and being present in each moment. 

4. In your opinion, what things in your life contribute most to your happiness and contentment? 

I’m a bit of a control freak, so I’m happiest and most content when I know that I am safe and secure. I enjoy knowing that there are ample resources and backup plans to cover whatever bumps in the road could come my way.  

I know that life isn’t always easy. I want to take full advantage of this chapter of life, and I want to be prepared for tougher chapters that I know will come along.  

I used to think that building wealth was about getting rich. Now, I know that building wealth and a lifestyle that provides freedom is about reducing the panic and trauma that comes with the difficult chapters of life. 

I’m sure I will experience external circumstances that will kick me in the teeth through no fault of my own. I’m content knowing that I’ve put myself in a position where I could deal with the issue at hand without creating a financial emergence or excess stress. Because of wealth and time freedom, I am more resilient. I will have an easier time navigating a difficult chapter and getting back to a positive place. 

5. How did quitting your job to start your business impact your financial goals or timelines? 

I gave up the highest-paying job I’d had in my life to start a business that would allow me to work from anywhere. I assumed this would lengthen my timeline to reach FI. Spoiler… it hasn’t.  

Initially, I set my sights on building my business to the point where it covered all of my personal expenses and max out my Roth IRA and HSA. Because I have no debt and such a low cost of living, the business quickly met that goal and provided additional revenue for investing and saving.  

I didn’t know this when I started, but there are so many different ways to make money in the bookkeeping/accounting industry. Now, I’m in my second full year as a business owner, and I’m on pace to make more this year than I’ve ever made in my life. I’ve been able to increase my prices because of the value I’m adding to my clients, and I’m choosing to work hard for a few months of the year (because I want to, not because I have to).  

Initially, I thought this move would slow down my pursuit of FI. But, so far, I’m keeping pace and will likely exceed my original goals and timeline.  

6. What enabled you to quit your job and start your business?

There have been a series of deliberate decisions that have allowed me to do this.  

First, I got my financial house in order. I’m completely debt-free. A few years ago, I also downsized and was able to buy a property outright (without needing to take out a mortgage). Because of this and my location, I have a fairly low-cost lifestyle. I also hoarded cash into an F-You fund, so that I didn’t have to worry about my finances while building a new business.  

Additionally, my last W-2 job provided me with years of networking opportunities that helped me build my client base for my new business relatively quickly. Because of this, I didn’t have to tap into my F-You fund for very long before my business became profitable.  

The pandemic and the resulting virtual communication allowed me to start a location-independent business. I wish none of us had to have gone through the pandemic. But, it helped people get more comfortable with video technology and utilizing services that were never face-to-face in an office. I have several clients that I have been working with for over a year who I have never met face-to-face. Even if people live far away, location is no longer a constraint for people. As long as the work gets done, my clients don’t care if I’m in a cabin near a lake or in a condo on the beach.  

Another important factor was finding a husband that shares a similar vision for life. After my first marriage failed, I assumed I’d be single for the rest of my life. Then, I stumbled across a man whose dreams, goals, and lifestyle aligned closely with mine. We dated for over 3 years and got married in 2021. Because he fully understands my dreams and goals, he’s not only supportive but also propels me to greater heights with my business and FI goals. We have so many nerdy (and inspiring) conversations about business, investing, and living life on our own terms.  

Please note: By no means am I advocating for a divorce if your spouse isn’t on board with your FI dreams. I hope you can find a spouse who shares your dreams or get into closer alignment with your current spouse. It can make a tremendous impact. I am so blessed to have found my current husband, and I don’t take for granted how much he inspires me. His impact and influence in my life provide me with more feelings of freedom than I’ve ever had before.

7. Were there things in your life you adapted so you could continue to work toward your goals?

I’m always pivoting in one way or another. We downsized from a 1700 sq ft house in the suburbs to a 420 sq ft log cabin with a pole barn in the country. 

cabin log rural house

After several years of my screen printing business being a side hustle, I sold it so I could focus more on my new business. Plus, I no longer have to worry about customers and order fulfillment while I am snowbirding in the winter. 

I’ve also learned that I’m just as happy in a hammock in my backyard as I am in a lounge chair at an all-inclusive. If I never experience a super expensive vacation again, I’m okay with that.

8. How did your pursuit of FI help or hinder your decision to start your business?

My pursuit of FI helped this decision. Finding resources like The Fioneers blog, the Slow FI Enthusiasts Facebook Group, and the Choose FI podcast have opened my eyes. They gave me the courage to dream up the life I want and helped me figure out how to execute it.  

It’s so easy in our culture to get tunnel vision and think there’s only one way to do things. My Fi journey has introduced me to so many people who challenge the norm and live their own way. I find that inspiring and hope that my story will also inspire others.  

9. Why and when do you think someone might consider “downshifting?”

I’ve never been a great employee, especially at larger companies or organizations. I had a hard time understanding all the inefficiencies and red tape. If I couldn’t understand the why behind what I was being asked to do, I would struggle to stay positive and my desire to really work hard would wane. This was especially true when the why was “because we’ve always done it this way.”

If you feel similarly, I would suggest downshifting and starting your own virtual business. It provides the freedom to develop your own systems and processes. When you become more efficient, you can make money in less time. 

There are so many opportunities to retool skills and competencies within a few months that could provide a solid income. 

However, I have one caveat. If you want to start your own business to build lifestyle freedom, you must be willing and proficient at self-teaching and problem-solving. There’s no one to pass the buck to, and you have to figure things out yourself! 

I’ve started multiple businesses in my life. One was when I was broke and needed money. The other was when I had a solid F-You fund and no debt. I’d highly recommend waiting to quit your full-time job until you have a deceiving amount of cash saved to cover your personal expenses until the business grows. This will help you to reduce stress. 

10. What advice do you have for someone considering a similar decision?

If you want to start a business that will become your main source of income, spend ample time planning and researching your target market and the product or service you will provide. Make sure your business idea actually solves a problem or pain point for your segment of customers. I’ve seen people jump into a business without knowing who will buy their product or what the value is.  

Second, choose a business that you are passionate about. There are pieces of every business that feel like work, so make sure you choose something you’ll enjoy most of the time.  

As for traveling or “snowbirding,” a lot of Airbnb hosts will offer up to 50% discounts if you book for at least 30 days. Gulf Shores in February is considered the slow season, so we were able to rent a beachfront 2-bedroom condo for 5 weeks at the same price as a single week in the summer.  There are affordable ways to travel for long periods of time if you do your research and get creative. In the future, we want to head further south, but we probably won’t stay beachfront.  

Thank you, Kari, for sharing your story with us! 

There are so many awesome things I want to emphasize from this interview. 

First, I love that Kari learned about lifestyle entrepreneurship 10 years ago! I recently learned the term and knew it was exactly what I wanted. When you build a lifestyle business, you are not primarily focused on growth and scale, which goes against the grain in the business world. Instead, you are focused on generating “enough” (whatever that means for you in your family) and doing it in a way that provides maximum flexibility and freedom to design the life you want.   

For Kari, this is a business that allows her to work from anywhere and to scale her hours up or down over the course of the year. My vision is similar. I want to be location independent, but not necessarily to be a snow-bird. I want to be able to travel for 3-6 months/year in our campervan or internationally. Additionally, I never want to work more than part-time hours, so that I can continue to focus on my health and well-being, relationships, and having fun adventures.  

Many people think that if they take the leap to entrepreneurship that they’ll generate significantly lower incomes, and it’ll impact their FI timelines. This wasn’t true for Kari (and so many other entrepreneurs). While businesses can take time to build, Kari is on track to generate more income than she’s ever made in a traditional job while working less and living her ideal lifestyle. Bravo, Kari! 

When I became an entrepreneur, I was worried about the significant pay cut as well. The reality was that in my first year, I generated quite a bit more income than I made in my part-time job the year before. While I’m not yet matching my highest-earning years, it’s likely to get there over the next few years.  

Lastly, I want to reflect on Kari’s insights about happiness and contentment. It’s very prudent to expect bad things to happen in our lives, no matter what our situation is. We could get sick or injured. We might need to become a caretaker for a loved one. People could experience the death of a loved one or a divorce. For Kari, building financial freedom and lifestyle flexibility adds additional tools to her toolbelt for when things like this arise. This allows her to be confident in her ability to be resilient in the face of challenges.  

If you’d like to stay in touch with Kari and continue following her journey, you can find her at: 

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