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Milestones for the Middle-Aged Parent

Remember when you were young and you had a pretty good sense of the boxes you wanted to check off? Those big milestones? The ones most of your peers also shared?

Graduate high school. Check. Get a degree. Check. Get a job. Check. Get married. Check. Have babies. Check.

What's next? Retirement? Death?

After we have children, our milestones often shift to their accomplishments. (Weaning, starting school, graduation, marrying them off, becoming a grandparent.) As parents, of course we take pride and even some ownership over the accomplishments of our children, but by focusing so much on their goals, we've often forgotten to keep crafting our own.

Between having children and settling into retirement, there are usually many, many years. How we choose to go about filling those years can have a great impact on our personal and professional fulfillment.

This year, I will be turning 40. I have two children in school. I've started a career that is growing. The question of milestones has been keeping me awake at night. How do I keep myself challenged? Passionate? How do I make sure that I continue to grow? How do I set real milestones that push me forward?

Some people have bucket lists. The problem with bucket lists, is they often carry about the same significance as a new year's resolution. It would be great to follow through, but I probably won't, and nobody will hold me accountable either way.

A milestone is a rite of passage. Something that you feel you must accomplish to truly feel satisfied with your life. A milestone is a significant step forward in life.

I suggest that at this stage in our lives, we view milestones not as things to do, but as ways to experience ourselves and fulfill our deeper needs and our greater contributions.

To help think through what these kind of milestones could look like, try this exercise:

Fast forward your life to the very end (morbid, but go with me...). What are people saying about you? What is the legacy that you have left behind? Think beyond children and career. Who is the YOU that your loved ones are mourning? What would you want them to say?

She always found a way to help those in need; She always challenged those around her to push themselves; He always emitted joy and lifted others up; He never held a grudge; She devoted herself to X cause...

If those legacies become the ultimate goal, what are the milestones that you can set up to reach them? Here are some milestone examples that my clients have come up with:

  • Begin seeing a therapist to address the issues that I've been putting off.

  • Commit a certain number of hours per month to being more involved in X cause.

  • Have a difficult conversation with a family member to reignite a lost relationship.

  • Overhaul my nutrition and exercise regiment to address health issues that have appeared in my life.

  • Make a career transition to an area that has always intrigued me, but scared me.

To take these from resolutions to milestones, you must set up an accountability process. Borrowing from the Strengths Strategy Coaching Toolkit (, I believe the ACT model is a great way to ensure your own accountability.

Assessable—The milestone must be measurable. How will you know you’re successful? How will you log and track success? This is about quantifying the outcome of your milestone, finding a measurement that can help you measure success.

Clear—The milestone must be clear to you and anyone you share it with. What is it, specifically, that are you going to do? Get as specific about what the outcome will be as you can. (It should be as simple as "graduate" and "get married" was once upon a time.)

Time-bound—The action must be time-bound. What is the deadline for you to complete this action? Most importantly - who will you account to? You must share this milestone with others who will push you and hold you accountable. (a friend, a therapist, a coach, a spouse...)

Lastly, I would add that milestones change and that's OK. I have friends who shared the same milestones as me growing up and have come to realize that as they progressed through life, they no longer held those milestones dear. Graduation wasn't as important as pursuing a career they loved. Marriage was no longer something they desired. Children were not necessarily a life goal or they found fulfillment in becoming a step parent. It is important to reassess and reexamine milestones, but holding them as a map or guide can support our intellectual stimulation as we continue into our later years, filling our time with purpose and fulfillment - and not just marching on towards that final milestone.

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