Spending just a few minutes on these journal prompts might be one of the best non-financial investments you can make in or before retirement. Clients who spend time in reflection and introspection find the transition into retirement easier and more fulfilling.

You might have heard that there are five stages in retirement, the third one being a letdown stage that leaves you wondering, “Is this all there is?” But that can be avoided.

Many of these journal prompts are based on the three essentials of a successful retirement – creativity, curiosity, and contribution. Get out your journal or a piece of paper to write down your answers as we go.

Prompt #1

If you’re not retired yet, the prompt is: what can you do in retirement that you can’t do now? If you’re already retired: what do you wish you could do more of right now? If you’ve got the time and the space, what do you wish you could do more of? It might have been a while since you’ve had time to explore the things you find interesting. In retirement now, you don’t want to just sit around all day and do nothing. You want to stay engaged and continue to grow and explore new curiosities.

A few questions under this first prompt to get the wheels turning.

What do you desire to learn more about? When you walk into a bookstore, where’s the first place that you go? Is it the self-help section? Or maybe it’s history, biography, or maybe cooking? What are the topics that you find interesting or even fascinating? What do you look forward to doing? It could be as simple as grabbing a cup of coffee with a new connection or an old friend. Next, when was the last time that you felt truly excited about something? What do you love to do? 

What did you do in your youth? Was there a hobby or an interest that you really enjoyed? Spend time exploring those curiosities that you had and get reacquainted with your early passions.

Prompt #2

Prompt two is all about connection: who do I desire to build stronger connections with? Maybe it’s friends, family, God, or whoever it might be. We have this client in his fifties, and in his first few months into retirement, he got reacquainted with a close friend from college. Like many of us, they lost touch once they started having families and working, but it’s like they picked up from where they left off.

Prompt #3

The next prompt is: what am I going to miss from my current employment? If you’re already retired: what do you miss about employment? One of the benefits of having your own business or being employed is that you’ve got these built-in deadlines and challenges you’re striving for each week, and those things actually promote healthy brain activity and development in retirement.

Think about what else you might miss about employment. It could be the social connections. That’s a big one because there are built-in social connections at work, and in retirement, that group kind of disappears. It might be that feeling of not having forward progress. If that’s the case, a good question to ask is, what did you make progress on today that made today better than yesterday? I really like answering that at the end of the day. The second question to that is, what could make tomorrow better than today? This can make sure that your future is always bigger than your past.

Something clients bring up under this prompt is missing the feeling of helping others in their work; contributing to a team or to the lives of others. Think about the causes in the world now that are really doing good, or think about the things that are happening in the world that break your heart. Are there any causes or charities that are helping alleviate that pain? 

Prompt #4

The next journal prompt is: who have you seen retire in your life? This is using the idea of modeling success. If we want to be successful, find someone who’s already achieved the results that we want and emulate what they did.
If you can’t think of anyone specific, ask yourself: if I saw someone else living their ideal retirement in an ideal way, what would they be doing? What about someone who has not retired well? What are they doing that is making it not great? What should you avoid? I created a whole video on this about creating your anti-vision for retirement, which most people do not do, but it can be really helpful as another exercise in association with these journal prompts.

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Disclosures: Securities offered through LaSalle St. Securities LLC (LSS), member FINRA/SIPC. Advisory services offered through LaSalle St. Investment Advisors LLC (LSIA), a Registered Investment Advisor. Streamline Financial Services is not affiliated with LSS or LSIA. LSS is affiliated with LSIA.