Thinking of retirement? Here is what I learned after 37-year career at a Big Four professional services firm.

My alarm rings—oh wait—I did not need to set it. Wow—I am retired, and I have nothing to do. Pickleball? Golf? Looking for another job? I will figure it out after my first cup of coffee. Actually, that was not how my first morning went, although it is for many who get caught unprepared or think that retirement is about finally having the time to do what we want or just do nothing at all.

In fact, the morning after my retirement party was just as I had planned it over a year earlier. Not just the first day; I had a written blueprint on what I dubbed in my farewell post on Linked-in as my next “Chapter One” after a 37-year “Introduction” to my life and career.

Looking back, that was some tough talk. Now that I am six months into my “Chapter One” – did it go how I expected? Would I have done anything differently? To cut to the chase, I feel like I exceeded my already high expectations and have never felt more alive, present, and forward-looking. However, the path to the present was a journey with many pivots.

Listen—we only retire once or twice in our lifetime—we should all do it the best we can for ourselves and our loved ones. This brief article summarizes my lessons learned so that perhaps I can inspire you to take it to the next level when your time comes—and it will.

Embracing the Drive: A Lifetime of Productivity and Pursuit

First, let me provide a little background. I am very goal-driven; I love to be busy juggling many projects. I have had a lifelong obsession with productivity, implementing productivity hacks from many gurus. I complain as much when I am busy as when I am not. I am also one of those “I work better under pressure” people, and I know I am not alone.

Right out of college, I joined a large multinational accounting firm and progressed to senior partner accustomed to handling ever-increasing responsibilities. My firm also has a mandatory retirement age of 60, so my big day did not come as a shock; it was a date I had considered in my entire career. I once had a goal to retire at 50, then 55 – to show that I could leave on my own terms – but as typical with my personality – I had to make my point leaving at 59 ½.

10 Things I Learned After the Transition to Retirement

1 – There is no one-size-fits-all to retirement.

I learned this during self-imposed brainstorming years before my retirement date. One day, I felt that I had earned the right to do nothing professionally and enjoy everything I had never had the “time” to do, like finally learning to play golf or travel to exotic places without caring about proper internet. I even downloaded “Learning Italian in your car” a few years back in preparation.

In the next brainstorming session, I flip-flopped. I needed to continue my professional career, and golf can wait until I am older – 65 or 70. I will still have a good ten years left – right? Maybe I will become a CFO or start my own company as a consultant. The third session went in a different direction – a life of contribution – I have been so blessed, and it is my time to give back by mentoring students and serving on charitable boards.

I needed help. So, I decided to speak to old friends who retired over the years from my firm. I would like to say this was a game changer, but at first, not really – it mirrored my brainstorm of options – one embarked on what she called “Immersive travel,” where they go away for months at a time, learn the language (good thing I purchased that Italian course), and embrace the culture.

One became the swimming pool warden at a 55+ community in Florida, ensuring no splashing and enforcing about 25 other rules. Others decided to jump right back into paid work—as an accounting or tax partner. What I noticed, however, is they were all happy. The decision was personal and a long and painful road for some, but they finally hit their own destination and never looked back.

So, I was back to where I started—a great list of things I could do that all appealed to me, depending on the day. The lesson I learned is that the answer is deeply personal and different for each of us. The more important lesson is to start the blueprint process way before retirement, leading me to the second related lesson….

2 – You can change your mind as many times as you want.

This is your journey. No one is keeping score. There is no wrong answer; you can pivot as often as you want. It is critical to understand this early and upfront. I found that being “retired” is an excellent cover for doing different things with no set pattern. “Hey, I am retired”.

If immersive pickleball in your 55 and over community is not fulfilling you the way you expected – maybe start drafting your AI start-up investor deck tomorrow. You can make this change. No one is keeping score except you.

3 – It is OK not to have an answer to the question – “so what are you going to do?”

The retirement date is approaching, brainstorming is done, and you have the outlines of an initial blueprint. Please do not feel like you must share this plan with all who ask this tedious and annoying question of what you will do. Do not offer to e-mail your complex Gantt chart to accompany your 12-minute response.

Why? Your plan may change—in fact, I hope it will (see Lesson 2). Most people just ask questions to be polite. I quickly realized this after the 100th time I responded with even longer than 12-minute responses. I realized I was answering these questions at length for my benefit—proving to myself that I still have worth and I do have a plan.

I finally stopped and just enjoyed saying things like “working on a few exciting things and will get back to everyone when they are firmed up” or simply “just things I really want to do.” Your real plan only matters to you.

4 – Plans can and will change, but at least have a definitive plan for day one.

The retirement party is over – what am I going to do tomorrow? In my case, I overthought it, but I don’t regret it. A full year before retirement day, I leased an inexpensive workspace in a co-working facility. I made new friends and brought my “work from home” days to a new level.

So going to this outside office on the first day of my new life felt comfortable and was already part of my routine – my favorite coffee and all. I grabbed my bullet journal and made it an early start to tackle my top three MITs (Most Important Tasks for my fellow productivity lovers).

I went for a pre-scheduled lunch with my wife at a waterfront restaurant and a couple of planned afternoon meetings. That was day one of retirement – it felt great, productive, and comfortable. I felt I was off to a good start.

5  – There is freedom in a routine.

I decided to keep many of my routines set over the last 37 years but with some modifications. I could have smashed the alarm clock and gone with my well-deserved new relaxed flow – but that was not me. Even retirees are allowed in the “5 am club”.

I continue to wake up early and plan my day with set outcomes aligned with my “new” goals. I even continue to dress up with a collared shirt and real shoes. No sports jacket, but I did consider it—I am retired…. I did modify my routine to allow for more consistent exercise (no more excuses), golf practice (new hobby) and other items important to me that I wanted to do consistently.

To stay on top of my industry, I always had “study and research” blocks in my calendar to keep abreast of things related to my career. The topics may have changed—less accounting and regulatory matters and more focus on entrepreneurship, IPOs, current issues facing a board of directors, etc.

The lesson here is to set your routine with things you love or don’t love but are important to you – i.e., health, well-being, education, etc. This gave me the needed structure and a foundation to structure my days. This also gave me unimagined freedom as I knew I was getting what I deemed important actually done.

6 – Make retirement work for you based on your goals and life plan.

As the months went on, I found myself making changes – some small and some very large. One example is the workday. We all were expected to accept an 8-hour workday (or more). I had to prepare weekly timesheets for billing my entire career.

I have quickly evolved to what I call a Power Four workday. I schedule and block four hours with a clear set of well-thought-out outcomes, such as writing this article or preparing an IPO readiness presentation. These daily tasks are preset the night before. After these outcomes are completed, I am free to do what I want—exercise, walk the dog, and, shockingly, voluntarily work a few more hours on work projects.

The lesson is that I set the rules that work for me. This lesson could have been learned pre-retirement, but the new realization is that these are now my goals and aspirations—not my old firm’s or someone else’s agenda. Big difference. Big lesson.

7 – Be ready for the “So what do you do?” question when meeting new acquaintances.

This relates to lesson #3 above but has a different twist. For most of my life, I used to say, “I am a partner at X firm.” So, what happens after you retire? “I am a retired partner at X firm?” Does not sound so great. I learned—albeit too late—that work is and was not my identity.

We are all the same person the day after retirement or leaving our jobs as we were on the payroll. The better question is – who are you? This can be answered in many fun and personal ways, and I wish I could go back while I was young and starting my career. Instead of being a CPA or senior partner at X Firm, I could be “a student of life,” a “champion of entrepreneurship,” or anything else. This should also be on your LinkedIn profile.

8 – Network, network, network.

I always focused on and nurtured my professional network. My network came through for me post-retirement. Both by sending me opportunities, offering to be a reference, and just offering to take me to lunch to see how I was doing.

However, I could have done better here. The lesson I learned about my network is that I should have taken steps to align it with my future self. My network was substantially as a partner in a professional services firm. I should have been more intentional about expanding my network to cover my post-retirement blueprint.

A strong network is critical, which goes without saying—the definition should be broadened to cover our entire lives pre- and post-retirement.

9 – Be open to opportunities, but learn to say no!

The blueprint I referred to was very helpful and was instrumental in my transition. However, to continue with Lesson #4, your plan will and should change from Day one. Opportunities will come – some great and some not so great. Saying “yes” (and not saying “no” more quickly) was my initial problem.

First, I wanted more than anything to have an answer to what I would do in retirement (Lesson 3). My identity was my work (Lesson 7), and it was going away. The drive to say yes to things coming my way was overwhelming. Opportunities are suitable for the ego but horrible when living a new life on our own terms.

You must pause and evaluate, even start with an assumed “no” answer. The “yes” must be overwhelming – not the fear of saying “no.” I would have failed here had it not been for a mentor. He understood what I was going through and knew I wanted to say “yes” to everything – so he stepped in and offered to be my sounding board before I was allowed to agree to anything.

10 – Finally, ask yourself – does what I am doing make me happy?

If no – make a change. If yes, do more of it by cutting things that are unintentionally creeping in. This is where I am today. I am busy. But unlike a formal career, living our own purpose, no matter what, in retirement is a different game.

We control more of our time and focus than was previously thought possible. I recently found myself waking up earlier with some pressure to get certain things done that I was putting off. Procrastination may be normal and expected (admit it or not) in a regular work life but not in retirement.

One of my new routines is journaling (a quick and easy method to see how I did and how I can do better tomorrow). I now catch this procrastination very quickly and evaluate why. In eight out of ten cases, I stop doing that task or project with instant relief (some things in life we will always need to do -like it or not – but those are only the remaining two items). So, I am constantly pivoting in a direction that makes me happy and gets me back to the feeling of wanting to get going every day.

Build your retirement to fit your individual needs.

The key takeaway from this article is that there is no correct answer. Have your initial blueprint way in advance, expand your network to cover your future self, and plan your first day. It is okay to pivot from there by being open to new opportunities as they arise. Don’t look at others, but evaluate from within and make your own personal changes. Be happy and enjoy life – it is an iterative process and an amazing journey.

**Mike Portegello is a retired Partner Ernst & Young 


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