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When is the right time to think about the next thing?

November 27, 2020

Retirement is talked about as a destination. “When I get there” or “When I am ready” then I will figure it out. It reminds me of my vacation planning. When my kids were in school, vacation was planned in sync with the school’s calendar. I didn’t start with an idea, we had dates. Most of the time that resulted with last minute planning and, mostly forgettable memories. There were some vacations which started as ideas that we fit into those windows. These were more memorable.

There was the trip to Paris for my daughter’s sweet sixteen birthday, a trip to explore Colorado for a week and the graduation gifts which had months of planning preceding each event. They required research, many conversations about what to do, and finally crafting the itinerary and plan. This groundwork opened up experiences that exceeded our expectations.

What has your history with vacations been? What about the last moves with your job or in your life? How many of these were responses to the unexpected or last-minute scrambles? Do you have any experiences with vacations or job changes in which you made a plan well in advance and you could feel the moment building? It is a strikingly different experience. Why don’t we do more planning?

Secret to Happiness vs Disappointment

There are probably three major reasons why planning is avoided. Life or work demands and compels our attention. The urgency of the moment or our uncertainty about our life command our full attention robbing us of time to think and dream about what we would want to do.

The second possible reason is our lack of resources or tools. We don’t feel there is enough money to take a vacation, or I don’t know how to do any other job, or no one would want me. Any of these cause us to be defeated before even trying.

The third possible reason is it takes time and energy to plan. Sometimes plans don’t work out resulting in disappointment. We don’t want to expend the energy if in the end it won’t happen. So, we are defeated before we even begin, so we look to the menu on the TV for what is on tonight.

Regardless of the reason, it takes effort, imagination, and a desire for something better. Most of us know how to work and get to a result, so this is rarely the issue. I would also suggest everyone has a desire for something better. Even those who are thrilled with their current lives have room for things to be even better. So, it really comes down to our willingness to dream. Our willingness to flirt with our desires and the risk of being disappointed. For many of us, dreaming and imagination are what we encourage our children to do. We however speak of it as folly for ourselves. If you spend too much time dreaming you will set yourself up for disappointment. This is what stops us.

Dreaming and disappointment are directly linked. They are related. The relationship is between joy and disappointment. You can’t have one without the other. Neither will exist without expectation. Expectation is developed through dreaming and imagination. The texture of a life avoiding disappointment is closely linked with avoiding dreaming and as a result very limited in a sense of joy. We will end up in this spiral, if we don’t trust or believe in ourselves. The good news is, what we dare to imagine or dream, in most cases, is within our reach.

First is to create time to dream. Next time you allow yourself to dream, allow yourself to think about how you could make this happen? Think about what I know, who I know, and what do I need to make some version of this dream become real. It’s time to reintroduce yourself to that dreamer. This is how you build a life that you will enjoy and change retirement from a destination into a way of living.