My Retirement Journey: From Trials and Tribulations to Triumphs

For many years prior to my retirement I dreamt about what it would be like. I imagine most people dream of retirement and believe it will bring immediate happiness. For me, in some ways that was true, but I learned that finding happiness after retiring a lifetime’s long career takes work, self-reflection, and intent. Growing up in a North Bronx area in the 60’s I had been working since I was in high school, with my first job as a shoe salesman. I worked through college and immediately upon graduation, I suited up, and entered the corporate world. If I add it all up, it comes to 48 years, and almost all of my adult life. In my career, I held about 5 different jobs, before my last job at AT&T overseeing a team of talented technical and business professionals. Among these jobs, some I absolutely loved, other times I had jobs that paid the bills to support my family so we could live in more financially stable conditions than I grew up in.

Throughout my career, I traveled quite often, sacrificed nights tucking my kids into bed and reading the bedtime story. Retirement was so far in the future I never gave it a second thought. But fast-forwarding to today, my kids have careers and kids of their own and I am a proud grandfather of 3 special young grandchildren.

Two years ago, my retirement party marked the end of my career with fanfare. I got the quintessential watch and plaque from my team, a large family brunch with gifts ranging from “old fart” t-shirts, to personalized golf swag, to a handmade journal where I expected I’d spend time reflecting during much of my newfound free time. But after the party, a loneliness set in. After 48 years on the go, working with purpose nearly every day, I found an emptiness I had not yet learned how to cope with. Some days were slow, bordering on boring. There were (and still are) times I miss the interaction among the people I worked with. I miss the challenge of making the right decision at the right time, and basking in successful outcomes. The pressure of managing people, being responsible for their continued growth and success, has been lost. These are all examples of the downsides of retirement.

What I have found and consider critical is having someone to talk to, a friend, a relative, a therapist. Someone who you can share with and who will not make any value judgements about what you are doing, or who you have become or who you are. For me, one of the most critical people in my life these days is, in fact, my therapist. There are so many good days in retirement, but help with the bad days is paramount to my successful retirement.

With the help of my therapist, I’ve learned tools and explored resources to reflect, intentionally think about what my goals, passions, and purpose in this new life stage are, called Retirement. As I look towards the future, retirement offers me so much more than I ever could have imagined. It allows me to see my grandkids more, watch them grow, and help them find their own way. I now travel for pleasure more often, without the stresses of stepping away from my work for a few days. I do more of what I love; writing, reading, and playing golf. Time is no longer my enemy. If I stay healthy, I have all the time in the world, to enjoy retirement, enjoy my spouse, my kids, and my grandkids.

Summarizing with Tips:

As you begin to contemplate retirement, you can do some of the following to be better prepared:

  1. Secure your finances. Ensure you meet with a financial advisor to determine how much money you will require after you retire, and where that money will come from. Work through any pensions, 401ks, Social Security or other income sources. Financial security is good for mental health.
  2. Stay engaged. Think about what you want to do in retirement. Whether it’s hobbies, travel, time with family, peace and quiet, volunteer work, or even a ‘retirement job,’ make sure to keep your mind sharp and spirits high.
  3. Seek help when needed. Family and friends are great resources, and often a great place to get support. But it is also important to have a professional and neutral perspective who can help you work through your life transitions.

On Therapy

In my opinion, an important person in your retired life is your therapist. Therapy has its cost, but the benefits far outweigh any such costs (and in many cases Medicare will cover the expense). So long as you define  hese costs in your financial plan, you will be fine. You will most likely want and need someone to talk to who is not related to you to, who can give you an unbiased perspective. There will be good days, there might be some tough days, your therapist can help with both.

If you are seeking professional support, consider engaging with a therapist prior to, and within a few months post retirement. Waiting until you begin to experience the emotions of retirement is certainly acceptable, but I found starting early (before I retired) and sticking with counseling is a good approach.

It is time to make it happen. I hope me sharing my experience may help you along your way to a happy and successful retirement. These years ahead should become the best years of your life.

This story is brought to you by Inner Clarity.

At Inner Clarity, we have a growing team of therapists here to support you. Currently, several therapists at our practice including Licensed Clinical Social Workers, Rebecca Sidotti, and Charlene Kwinter both accept Medicare Insurance. We also have a broad network of community resources and can work with you on your individual retirement journey. Get started today at