There to Here - What's Next?


Making a major life decision doesn't happen overnight … at least for us it didn't. Some things were a certainty. Owning a business and working 60-70 hours a week was exhausting and couldn't go on forever. We didn't have enough savings or investments to retire and we still had kids in school who would soon be heading off to college. We hadn't made any definitive decisions. We wrestled constantly with what should come next. How do people change the course of their lives? What needs to happen?

All the land anchors kept us shackled!

All the land anchors kept us shackled!

One long, “just us” weekend, we explored our options. Here, we were in our mid-40s and the clock was ticking. Whatever we decided to do in the future, there were certain things that needed to happen ... sooner rather than later. We were feeling shackled. We needed to sell the company. We needed to divest ourselves of what we'd later come to call “land anchors” … a big house with a big mortgage, expensive cars and lots and lots of “stuff”. We needed to simplify our lives. We could decide what to do once we had started the simplification process, but we were convinced that this downsizing was the path to our future.

Within that year, we sold our company and the big house. We moved to Wisconsin, bought another house for 1/3 the price of the Colorado house and began working for our new owners, to whom we had made a 3-year commitment. The weight that was lifted from our shoulders was enormous. We still worked hard and long, but there seemed like light at the end of the tunnel.

Now it was time to start thinking about what we wanted to do when we grew up. If we could do anything we wanted, what would we do? where would we go? what “next steps” would be necessary to get there? Starting our own company and running it for 10 years had been an arduous task, but it was an adventure. What would our next adventure be? Sitting home and knitting mittens was not an option. Travel has always been a major attraction for us, but you can’t travel all the time. Can you? Sailing is wonderful, but it’s a hobby, not a lifestyle. Right? But what if we really could sail off into the sunset?

These ongoing discussions prompted more questions than answers. Could we ever afford to live a life of sailing and travel? How much would we need if we wanted to retire early? How early? What about the kids? What about our future financial security? How could we possibly learn everything we needed to know about living on a boat and sailing? What if we sold up and sailed off and we didn’t like the liveaboard life? Worse yet, what if one of us liked it and the other didn’t?

We needed a plan. We needed a plan that explored all the questions and came up with as many viable answers as possible. Maybe some questions would need to be left unanswered for the time being, but we could make some reasonable assumptions. What did we need to do to make our dreams turn into our reality? We needed to set goals, but where to start? Well, as everyone knows, you start at the beginning. Let’s get it all down on paper. Let’s start with a 5-year plan and see where it leads us.

The decision itself was liberating. We enthusiastically set about our planning … in writing, in a separate, purposely-bought, 99-cent notebook ... over the next few months. We listed every little question and concern we could imagine. Finances now and 20 years from now, the kids and family, health, safety, learning to live aboard, sailing skills, boat repairs and maintenance, choosing a boat, timelines. What things needed to be accomplished, how could we accomplish them and when could we make this happen? The list seemed endless and the tasks insurmountable when taken as a whole. How could we possibly get our arms around this unwieldy list and such a complicated plan? Perhaps we should handle it the same way we handled long term projects in business? Break down the tasks into manageable, smaller goals over the next five years and make it work?

Click here for the next in the series: There to Here - The 5-year Plan Pt. 1