The Next New Job

People ask me what it feels like to be retired. The closest analogy I have come up with is that it is like the experience you have when you are pursuing a new job.

At one point in my career, I was preparing myself to compete for my first job in middle management. You could say that getting the job was sort of the pinnacle of my career. I had several other jobs after holding that position, but all the subsequent positions were offshoots of that first middle management job.

Before I got the middle management position, I spent literally years developing myself for consideration. I was doing all kinds of things to build my skills and to enhance my visibility within the organization. I wanted the folks above me to recognize my name and think of me as a strong candidate. More importantly, I wanted to have the talent and experience to actually BE a strong candidate. I was a first line manager for almost twenty years and I spent all that time growing my skillset.  I learned from my experience and from my leaders.  I tried to take the best of myself and my various managers to create a quirky cocktail of a leadership style that I employed in all my first line management positions.  When I began preparing for the next level in earnest, I took classes, read books, took on extra assignments, and put myself in challenging situations to grow my abilities. I applied for, was accepted into, and graduated from a “readiness” program- which is sort of like rush week and hazing for management jobs in my agency.   In short, trying to get the middle management job became nearly as much of a job as my “real” job at the time.

Ultimately, I succeeded. I competed for and got that first middle management position. There may not have been a ticker tape parade exactly, but there was celebration and rejoicing.  I seem to recall balloons being involved.  Everyone congratulated me and wished me much happiness. Colleagues and mentors who had been helping me in my development breathed a collective sigh of relief to finally be able to wash their hands of me and let me float on my own.  It was thrilling and I was quite giddy.

For the next several weeks, I became engrossed in the practicalities of getting a new job.  I finished up projects and tasks that I was doing in my current position.  I prepared the person who would be acting in that position until the agency selected a new permanent manager.  I packed my stuff and moved to the new office.  I did the administrivia necessary to get authorized on the new computer systems I would need in my new job.  I explored the lay of the land in my new office.

Once I completed all this “changing of the guard” work, I found myself in a difficult situation.  I had held the front line manager position, in one form or another, for such a long time.  I realized that I had become a master at it.  It wasn’t that it was easy for me or anything, but I certainly had developed a certain facility and confidence and momentum in executing my responsibilities on a day-to-day basis.  By the time I was selected for the target middle management position, it could even be said that I had become a master at the job of getting this job. Now that I had it and the novelty had worn off, I was back to square one. I was faced with the whole new challenge of actually having to DO the job!

All of sudden, “routine” tasks and decisions were not routine.  Instead of tumbling through a day of problem solving and getting things done, as I had for years in my front line management position, I found myself stumbling over each step because I found all the steps to be new to me.  The steps were all in unfamiliar places now, steeper, and made of different materials than I had experienced in my former job.   In my front line position, I easily contemplated the possible strategies for addressing each issue of the day and experimented with reasonable confidence that I would find a way to success.  In this new position, my mind felt tight and restricted when I tried to percolate new ideas.  The stakes were higher and I seemed to have less mental resources and agility to propel me towards success.  As certain as I had been that I would succeed as a first line manager, I was often as certain that I would fail as a middle manager.  After all, you can only use the excuse “I’m new” for a short time.  As I struggled with problem-solving and fueling effective operations, I was well aware that I couldn’t just try any strategies.  I had to try the right strategies to produce results.  I knew that, as some point, I would have to produce the results expected of me or I would have to face the fact that I had failed… no matter how hard I had worked or how many creative strategies I tried.

Retirement was kind of like that for me. I aspired to retirement for years. I thoughtfully and strategically set up my life to prepare myself to retire. When it finally happened, there was all manner of celebrating and well-wishing. For a few weeks, my life was a whirlwind of “getting set-up.” Just like when I changed jobs and had to deal with the pragmatics and tactics such as getting on necessary computer systems and arranging my office, I spent the beginning of my retirement packing and moving and making sure the processes of my new life were in place.

After that first flurry of activity, I came face to face with the same reality I did when I actually started my first middle management position. I had no real idea of how to “work” retirement on a day-to-day basis any more than I had any idea how to “work” the middle management job on a day-to-day basis.

It wasn’t that I was unhappy in either case or that I regretted my decisions to pursue the career-defining job or to retire. In both situations, I was excited and joyful. It is just that, in both situations, I was disoriented and lacked confidence that I would ultimately right my ship and sail somewhere wonderful.

In the middle management position, I may not have hung the moon and the stars, but I think I did succeed. I am proud of my little legacy.

As time passes in my retirement, I find myself experimenting with numerous strategies and approaches to craft a success of my retirement life. I think it is working. I am less disoriented and my confidence is growing all the time. I feel like I am clicking along well on all cylinders now.

I have learned that, in retirement, unlike in that next new job, the creative strategies I employ to succeed cannot fail as long as I satisfy myself.


So what do you think?  Did your retirement feel similar to transitioning to a new job?  Or was your experience different?  Please share your perspective by leaving a comment.  In the alternative, you an email me at Have an exciting (in a good way!) day!



8 thoughts on “The Next New Job”

  1. Very insightful! I have felt very much the past 2 years that I went from mastery to being a beginner. Besides figuring out a new day-to-day rhythm, I needed to figure out a new identity articulation, too. And since I did very little planning (unexpected early retirement), for me it was getting the “new job” a bit unprepared also. I do like your analogy.

    1. Hi Pat! Thanks for the comment. I’m such a fussbudget, I tend to obsess over everything. I can’t imagine how hard it would be to have to retire unexpectedly. You’re a braver soul than I am! Good for you.

  2. What an interesting write-up on the steps you went through to get to retirement. I worried when you progressed to middle management and on, that I was losing my connection with your strong ties. You were my source to continuing on in my position. But with your emails and cards from time to time, I felt a connection to you. Thanks for all your encouragement to my steps on, as well!

  3. So well said! Yes, we do prepare for retirement. But of course we don’t know what it’s like until we get there. I think it takes awhile for us to get our retirement “sea legs.” I’m one-and-a-half years into it and still finding my way to where I want to be. I have heard several people say it took them 2 or 3 years before they had fully settled in to a new lifestyle. Makes sense to me! The workplace is all-consuming, and therefore leaving it is disorienting. But that’s OK; we’ll find our way eventually and it will all be worth it. I love being retired.

  4. Excellent post Terri! I am newly retired…5 months and just today was feeling a little guilty about not accomplishing something everyday. Your insights have been most helpful. I signed up with a local gym and weekly training sessions…thinking I finally have the time to exercise, but I just don’t love it! I called today to cancel the weekly training sessions. I guess I’m not really ready for structure yet and instead spend my days enjoying my condo, the weather, my family and my cat. I’m sure I will get my groove eventually and just need to give myself time. I do love retirement though!!

    1. Welcome, Carol! Thanks for reading and commenting. I agree that you will find your own space and your own pace in Retirement World. Give yourself some time to rest and explore your new life. We tend to think we “should” do certain things, like exercize, that seem productive and worthy. I’d say that taking the time to decide what you want to do is absolutely productive and worthy. At the risk of being a little naughty, I’d advise you not to “should” all over yourself!😏☺️

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