Live Where You Want

We live in incredible times.

For workers and business owners who primarily work behind the keyboard or Zoom screen, there has never been a time that allowed for such geographical flexibility. Choosing where you live based on where you want to be and not because of the location requirements of an employer is a privilege. But like most great opportunities, it comes with great responsibility.

I was raised in Wisconsin and went to school in Maine. My wife and I lived in New York City for four years after graduating college before escaping to the freedom and outdoors of the West Coast. We have called the San Francisco Bay area home for the last four years, and our time in California has been magical. We can walk from our apartment to hundreds of hiking trails and biking routes. Even better, we’re a short drive from beaches, surfing, and the mountains. Some of the best skiing in the country is just four hours away! Anyone who hasn’t spent just a little time in California needs to pack their bags and come here immediately. The first beer is on me!

At the same time, as our life evolves, what we’re looking for in a home changes. We’ve become red-eye warriors. But taking red-eyes every time we want to see family is not ideal (especially when we have kids). Not to mention, the cost of living in the Bay Area is outrageous! Don’t get me wrong, it makes sense; this is a killer place to live and some of the most successful companies have called San Francisco home for the last 15 years.

However, without a major tech exit, life only gets more challenging here. With $4 million+ 3-bedroom homes, daycare at $50k+ a year, and high taxes, life is just expensive. For some, it may be worth it, but it’s not exactly the life that my wife and I are looking for. I was greatly impacted by the early death of my father and have a strong desire to spend as much time with my family as possible. I don’t want to miss out on life just to provide for my family.

As my wife and I have come to this realization over the past year, the pressure of deciding where we want to raise our family has become overwhelming. For one, how do you top all the great things about San Francisco? Secondly, we’re complete free agents. Almost all our family and friends are either in San Francisco or New York. My Mom lives in Cincinnati, and we have extended family in Michigan, but we’re not jumping on the opportunity to go back to a cold climate. We love the mountains and skiing, but the early mornings of shoveling driveways and dealing with cold winters doesn’t sound appealing. Because of our free-agent status and our willingness to move to a lot of different places, we almost have too many choices.

One of the things that makes this process so challenging is that we’re planning for a life that we haven’t experienced. We’ve lived the young-professional life in two big cities and now we’re trying to plan for family life. It’s basically impossible to have any idea what our needs are going to be like. Our family and friends have been great resources, but it’s hard to compare with real-life experience. Apart from finding a family-friendly place, we’re quite focused on community and access to nature. Apart from that, we live in a time where Amazon delivers everywhere in less than three days, and every town has good cocktails and tasty food.

I’ll talk in the future about our efforts to find our ideal home, and where we end up. But I wanted to reflect on how lucky we are to have the flexibility to choose our own destiny. While it may be challenging to find the right spot, it’s always better to have the choice than be forced into a suboptimal outcome.

As remote work continues to gain acceptance post-COVID, growth in 3rd – 5th tier cities will continue. You can’t argue with high quality of life at a significantly lower cost. Companies will have happier, harder-working employees.  

We have a solid leaning of where we want to end-up, but I’d love to hear from all of you. What factors should we take into consideration when choosing to move from the big city to a more family-orientated town? If you could do it all again, where would you end up?