Starting Over at 50 – Career Coaching / Life Coaching

Starting over at 50 - Thom Singer - Career CoachStarting over at 50 was the best thing I ever did. When I was growing up most people looked at fifty as old. It never appeared that way to me. My dad was 52-years-old when I was born and my early memories of him are after he turned sixty.  He was always active as a parent and a person. He golfed, bowled, went dancing with my mom, and coached my sports teams. People asked him why he seemed so much younger than his age, and he said he was starting over at 50 with a new baby. Now that I am involved in career coaching for people over 50, it is clear having something important is the key (no, I am not suggesting you have another kid).

As I got older I looked forward to having a little grey hair and always felt that one could start over at 50 (or any age). But as I got older I was not sure that I had reached my potential. It seemed that with every two steps forward I made in my career, there was one big step backwards. My corporate career had been successful, but I had my ladder against the wrong wall. I wanted to work for myself.  So in my 40s I took the leap.  Again, I did okay, but it was never easy for me.

I faced a choice.  Be positive or negative in how I lived the next half of my life.  I did not want to let the struggles win.  I had to make a strong decision to take control of my own life. I wanted to reinvent parts of myself (not all, I was doing great in many ways).  I just knew I had to start over at 50 so I could have more fun and enjoy the journey.

Make Age 50 to 75 The Best Years of Your Life

Life is not easy for anyone and we all have our struggles. As I approached my fiftieth birthday I was overweight and sluggish. I questioned my self-worth. My financial situation was not where I had dreamed it would be by this stage of my life.  The pressure of raising children were heavy on my shoulders, and my career had hit a plateau.  I was in a funk.

As all my high school and college friends came upon this 50th milestone, I witnessed many of them have the traditional midlife crisis. Several experienced depression. Some got divorced. It was not uncommon to hear negativity and a feeling that the best years were in the past. Although my life was not perfect, I decided I would make age 50 to 75 the best years of my life.

This was a big declaration, as overall I have lived a good life. But I did spend a lot of my time worried about what others might think, and doing the things that I thought were the “right” choices and not “my” choices. I knew I had make some changes, but starting over at 50 is not easy, as humans are creatures of habit.

Starting Over at 50 – Not Starting From Scratch

There was a lot written about people who lost everything and had to start over. However, there was not much on the subject of people who felt they were just coming up short of what was possible. I was not going to be starting from scratch, but I was going to reinvent my personal and professional life.

Once the decision was made to start over at 50, there was no turning back. I got excited about the next half of my life.  Half you ask? Well my dad did live to be 99 years old. Thus I have to plan accordingly.  Even if it will just be 25 or 30 years, that is a long time. I know people who accomplished amazing things in a decade (or less) of effort, so this leaves me a lot of options for success.

My first thing was to publicly announce that I was changing my life. A problem we face in our society is that people make decisions about who you are and what you are all about. When you make substantive changes, many of them go unnoticed.  I did not hide my excitement about the next phase of my life. I took control that I was about to take full ownership of managing my career potential.

Change Is Difficult

The one thing that became clear to me is that change is hard. Making a decision to start over at 50 means a commitment to doing a lot of things. We all have potential, but potential does not equal performance. To get results you have to take actions.  And for many people it is easy to do things for a short time, really changing takes above average dedication.

Embracing that I was going to have to work hard for two hand a half decades to keep my pledge seemed daunting. It is a lifetime. at the time I turned 50 my oldest daughter was twenty. Think about this, twenty years is a lifetime for a young adult. It was ages ago when I was 25.  How could I ever get to be 75?  Well it is going to happen (I hope), and if I want to look back with joy I needed to create a plan.

Moving Toward Potential

When I turned fifty I began an ongoing study of how people got closer to potential. The most interesting thing was realization that we don’t ever reach our potential. Our abilities change. We lean and grow all along the way. As we go through life our potential shifts and changes. If you are feeling lost because you are behind on reaching your potential, you are not alone. If you feel you have done all you can, you are selling yourself short.

To start over at 50 you have to identify what is holding you back. My work, which I call “The Paradox of Potential” centers around discovering what is holding you back and identifying what you need to do to move across the gap between your potential and the results you are achieving. Do not see your potential as a final destination, but instead as a target.

Try New Things – Starting Over at 50

The corner stone of my life for the last few years has been the mantra “Try New Things”. It has become clear to me that I spent much of my life doing things that came easy to me. I did not push myself. I stayed in my comfort zone. At 50 years old I changed all that. Part of my starting over at 50 has involved saying “YES” to activities in my personal and professional lives that are not easy.

Having always been a “city kid”, I now go hiking and camping. I am also planning an extended hike on the Appalachian Train in a few years. My fear of heights have kept me on terra firma. Recently I have gone zip lining in Costa Rica and at Pike Peak. Additionally I jumped off the SkyJump at the Stratosphere in Las Vegas.  Having never been an athlete, I took up running (talk about “starting over at 50″… this was difficult).  I learned to enjoy bourbon (after a life of beer and wine). There was that time I was an actor in a short movie, and I took up performing stand up comedy, an activity I had always wanted to try, but was too timid to attempt.

What are you trying that is new? If you try new things it pushes your view of the world. In working with others I have made this a focal point of our work. People who get comfortable trying new things do the best at starting over at 50.

Career Coaching / Life Coaching

Starting over at 50 has not been easy. I drift back into my old patterns with easy. I need to stay focused on enjoying the experiences and not being reactionary and scared of new actions. Having encouragement and accountability is key to making the changes you desire.

Finding a mentor or a coach is key. I have hired coaches and I have found mentors.  Both are good options.  (Mentors are not just for young people, we can find them at any stage of life). The trick is finding someone who can inspire you to do more than you would do alone. You want to make sure you admire the person and what they have done. I hired a coach who talked a good game, but really did not inspire me to be a better person. The coach was so sure she had the answers, that I felt that the advice was the same she gave all her clients. A career coach / life coach should be a guide and together you should uncover the right actions.

To be honest, I do not make a living as a coach. I only work with a few select people where there is a clear synergy.  I am also not “expensive” as I see my role of being a guide as not a way to just make money. My clients need to be people who are invested in the work and want to build a real friendship. Most coaches disappear after the transaction is over and the money stops. That is not my goal. I want to work on the project, and remain friends even when you stop paying me.

If you are seeking to begin starting over at 50 (career and life), and want a career coach, let’s talk. Because I do not do this work full time, and can only work with one or two people at any time. No coach is not the right fit for everyone, and I will not try to sell you on working with me there is no real connection.  We can talk about what you are looking to do and I will be honest if I can be a guide. Starting over at 50 is a cool thing to do.

Call me today!  (512) 970-0398 or thom (at) —


Thom Singer is a business motivational speaker and professional master of ceremonies.  He is the host of the “Cool Things Entrepreneurs Do” podcast and the author of 12 books.