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I was recently one of three finalists for the New Yorker magazine caption contest. Each week, over 5,000 entrants are submitted for an uncaptioned cartoon, and they cull the list down to three. I was really excited to be a finalist, and when the winner was announced … I didn't win. But whenever something doesn't go the way I had hoped, I always say to my wife, "Well, at least I'll get a column out of it." So here is how my caption contest experience relates to financial planning.

Mind map. When the contest cartoon appears in the magazine, I go in many directions for the caption. One of the ways I approach it is by writing down several concepts that could work and then picking the angle that I like the most. I encourage you to use this in your planning. For example, if you are thinking of moving, take a piece of paper and write in the middle of it: home. Then draw branches for everything that the concept of home brings up for you.

It may trigger a variety of options ranging from community to fireplace to backyard to bedrooms. There may be branches off each of those options. Backyard may have gardens or fence. When you have completed this, carefully look it over and determine which characteristics matter the most to you, and only look at homes that share those characteristics. This will help you avoid falling in love with a great home that doesn't match your objectives. Mind mapping lets you broaden your thinking before narrowing it, creating a range of possibilities before limiting them.

Sacrifice. I probably entered the caption contest 50 times before finally becoming a finalist. Now that I didn't win, I'll probably enter another 50 times to see if I can.

My wife had a children's book published several years ago. Many people come up to her with their idea for a children's book and want to know how she got hers published. She still has copies of the rejection letters she received from her efforts to get published. We often see the results without the effort.

The act of saving is a sacrifice. You are denying yourself something today so that you can have a better shot at what you want tomorrow. More importantly, by limiting your needs, you will require less money in the future because you are used to spending less. We know that spending on stuff does not bring as much satisfaction as spending on experiences. But spending can create some excitement.

One of the ways that you can substitute that feeling is this: When you avoid buying something that you don't need, write a check to your investment account, charity or vacation fund. The money was going to be gone anyway, but now it is serving a long-term purpose.

No regrets. When I found out I was a finalist, I posted a link to voting on my Facebook, Twitter and LinkedIn accounts. Not only did I get reinforcement from friends and peers for my efforts, but I wanted to give myself the best possible chance of winning. Even though I lost, I went down swinging. How many times do we stop ourselves from doing something because we are afraid of being disappointed, or, maybe worse, embarrassed?

Writer Sydney Harris said, "Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable."

One of the benefits of working with a financial planner is sharing your wishes with someone. This creates support and accountability. You can also do this with a trusted friend or mentor. Don't look back at your life wondering what could have been.

Grieve. I know a lot of people would say that just being a finalist for the contest was enough. In fact, that's what I said right up until I lost. It wasn't enough. I felt disappointed. Rather than say that you didn't really want something you didn't get, feel the sense of loss.

Rationalizing sidesteps learning. I see this all the time with clients who get divorced or miss out on a promotion or where life turns out differently than they had hoped. It is important to connect with how hard things are because only then can you move on. When you make someone else bad in order to be good, you end up holding on to destructive emotions far longer than if you face them.

Decide if it's worth it. My New Yorker experience is still new, but in spite of my disappointment, I enjoy playing with the captions.

For me, it's worth continuing to pursue the objective of winning the contest, no matter how unlikely it may be. But there are many things that we end up pursuing for reasons that are not our own.

Private schools for our kids, graduate education, that vacation home all may be things you have carefully evaluated and made a decision that it fits for your life. Or it may be something that you feel you should be doing, even though you really don't want to. You get to decide whether your actions and values align.

I may never win this caption contest, but I will learn from it.

Ross Levin is the chief executive and founder of Accredited Investors Wealth Management in Edina.