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We Sold Our House and Quit Our Jobs to Pursue Happiness — Here’s How

By Team Tomorrow
Published June 17, 2019

For years, my wife Jaime and I have talked about our dreams. Dreams of travel, entrepreneurship and of spending more time together and with our daughters.

But financial realities can make those dreams feel impossible to create. How do you take the leap on entrepreneurship while raising three young girls? How can you find the time to travel when you can’t take too many days off of work? How can you find more hours for your family while still paying the bills?

What if chasing your dreams means taking a financial step backward?

Last year, Jaime and I finally gathered the courage to choose to take a step backward with our money so we could take a step forward with our life. We sold our house, I parted ways with my 9-5 job and decided to spend a year of entrepreneurship and family time.

We went from a single-income household to a zero-income household. But we knew it was something we needed to try. We didn’t want to spend the rest of our lives wondering, what if?

Whether your dream is to leave your job to travel or change careers to something lower-paying but more rewarding, here are three ideas to help you manage when you take a leap.

Find Your Funding

The bills don’t stop when your employment does. Jaime and I knew we needed to have our expenses covered (with some buffer too) if we were going to take the big risk of entrepreneurship.

For years, we had been making additional payments on our mortgage with a goal of becoming completely debt free. Selling our house certainly wasn’t a conventional path to finding funding for our year of adventure, but it worked for us. We were willing to think differently about what our priorities were and saw the potential of our year of experimentation outweighing the life we had built in our home.

We also worked to create a solid budget for the year so we knew with confidence that we could make it through without having to pull from our other savings.

Know Your Goals – And Your Exit Strategy

Before you go in, have clear, realistic expectations of what you want to get out of your life change. Give yourself intermediate targets to shoot for and measure your progress along the way.

Keep tabs on your finances, but give yourself permission to put off worrying if you’re sticking with the plan. Even when you’re staying on-track with your budget, it can be challenging to see your account balances go down instead of up. Remember that you made a plan for this and you’re ok.

Also, go in with a plan on what it’d take for you to change back and how you’d do it. When I parted ways with my job, I left on good terms. I had built a solid network of coworkers and knew that if/when I were looking for a job again, I’d have people I could reach out to that would be willing to help.

Strengthen Your Support System

Making big life changes (even exciting ones) can create a lot of stress.

Before you take the leap, make sure you understand how your life change will affect your support systems.

You may get a lot of positive reinforcement out of interaction with your co-workers; leaving your job means finding new sources of reinforcement. You may find strength in the community you live in; moving may mean finding new friendships and anchors.

It’s important in any life change to manage not just the finances, but your emotions and mental state as well. After all, the whole reason you’re making the change is in the pursuit of something better!

Live Without Regret

Life’s an adventure that we only get to live once. Don’t be afraid to take some risks, make some changes and see what’s out there for you. Even if it means taking a financial step backward, you’ve got the opportunity to try for something better and that’s something you can carry with you the rest of your life.


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