NOT Failing as a Retiree

In her excellent book ‘Retirement Reinvention’ Robin Ryan lays out 5 points to help guide you to a ‘successful retirement’.

Reading these points was like Déjà vu for me. I went through the 5 points she mentions 10 years before she released them in her book. Because I didn’t have these ‘steps’ to guide me in the process my path was probably more difficult and more time consuming than it would have been if I’d had the book back then. I hope her book and me sharing my experience with you here will save you some time and perhaps give you a bit of inspiration.

If you’re like me I’m confident, you’ll find these points and my experience of going through them helpful. They will be especially helpful if you need, or want, to keep working into your retirement years and if you’re determined to do work you love while making sure you have time to do the ‘other things’ that add richness to your ‘Golden Years’.

“In fact, many people actually become a failed retiree. That is someone who is depressed
with long days ahead and no fun or meaningful activities that they partake in.”
Robin Ryan

This path, the path I followed long before Robin laid down the crumb trail for us to follow in her excellent book, this is the path to an incredible, successful, retirement… even, and perhaps especially, if money is tight.

Let’s explore the 5 steps…

1. Develop a Life Plan. Here’s how I did it and at the time I didn’t even know I was doing it.

I sat and thought. I had a living room, a family room and an office, but it was a chair in the garage that I most remember sitting in. It was a comfortable stuffed chair out by the dart board and I’d sit there for hours in the early mornings and evenings during the Spring, Summer & Fall.

The months slipped past as I tried to imagine a future that would work for me.

  • What could I do next?
  • How could I earn the income I wanted and needed?
  • What income-producing activity would fit my self-image?
  • What would allow me to do things that challenged me, fulfilled me and produced a nice income?

This was a tall order. I was in my fifties. I had a fun, outwardly successful career, but a few bad business decisions had left me with a negative net worth.

I’d been broke before and my self-esteem was a bit better off this time than it was 15 years earlier but I was still a bit broken and very unsettled.

I’m not sure if anyone would hire me but it really didn’t much matter much anyway… I just couldn’t see myself working a ‘regular job’. I’d been self-employed for too long… I would gladly work 50 or 60 or more hours per week to not have a 40-hour a week job. Strange I know, but none-the-less true.

I also wanted the freedom and ‘big-win’ potential that comes with self-employment.

My age played a part in my need to find a ‘new thing’ and I was determined to find a new thing that I could do forever.

My ‘life plan’ was beginning to shape up. I wanted to continue working for myself. I wanted to leverage what I had learned from 30 years as a ‘marketing guy’ including 20 years of which I was also a professional speaker. Yet I wanted to do something entirely new and different.

I didn’t really want to provide services, at least not marketing services. I wanted to apply my marketing talents to my own products or services.

I wanted to continue to challenge myself and have new experiences.

But what? What would I actually do? What product or service would I provide?

I found my ‘life plan’ was being shaped by what I was NOT interested in, or willing to do, as much as by… what I wanted to do.

I needed to find something I could offer, something I could sell, that I would love providing… something that I could get excited about.

Again, long before I had heard of Ryan’s list, in fact, more than a decade before she had written it, I found myself slipping from #1 on her list, from developing my Life Plan to #2… Exploring a Hobby.

2. Explore a hobby. Again, this was another fairly long process, made even longer because my favorite ‘hobby’, the one thought that I just couldn’t shake as I was thinking, involved me wearing a costume and working (as a volunteer) only 1 month per year, and only a few days out of that month.

Yes, the hobby I most loved was portraying Santa Claus.

I loved it, but there were some inherent and very obvious problems with even thinking about turning this hobby into a business that would earn any meaningful income… let alone a full-time annual income.

Enter a process that you might really benefit from… it’s called asking Empowering Questions.

Many years ago, I owned a seminar promotion company and the motivational speaker Tony Robbins was a client of mine. During the years Tony was a client I attended dozens of his seminars and spent a fair amount of personal time with him. One of the things he taught and used was this concept of asking ‘empowering questions’.

It made sense to me and I developed the habit and I’ve been using the process for over 30 years now.

It takes some time and practice to craft the questions in ways that best serve you, here are a couple of examples.

  • If there was a way to be a well-paid, full-time, year-round, Santa Claus what would it be?
  • If there was a way to earn a full-time income during the Santa season what would that look like?
  • What ‘other’ opportunities are there for a professional Santa Claus?
  • Have others Santas done what I’m hoping to do?

Do you see what I’m doing here? I’m forcing myself to think outside of the box.

I spent months thinking about how I could earn a nice, full-time, income portraying Santa Claus. Eventually, the answers started to come. At first, they came to me in fits & starts. I would try something and that would spawn a new idea, and that yet another idea.

Another thing that’s kind of eerie is how I would get an idea for something and in the days following I would get an inquiry to do the exact thing I had just thought of… seriously, I could tell you stories that would make your hair stand up.

Looking back, it seems like I was following Robin’s formula like a recipe.

3. Learn something new. As my Santa plan was developing I realized there were some opportunities that could be fun and financially lucrative, opportunities that also aligned with my self-image… like acting, appearing in TV commercials, TV shows, and movies.

I had never acted a day in my life, not even in school plays and I didn’t know a soul in Hollywood. I definitely would need to learn some new things if I was going to follow that path.

Another opportunity that sprung from my ‘empowering questions’ was being a ‘brand ambassador’. This is one that just fell in my lap and one where some of my prior experience transferred and still there was much to learn.

There was working with photographers for ‘off-season’ photoshoots.

Each of these required me to learn new things and that really excited me… I began to think, ‘this could really happen’, and it did. 

4. Give back. For 8 years my ‘Santa portrayal’ was an act of community service. I was a volunteer and it filled my soul.

There was a part of me that felt strange about accepting money to ‘be’ Santa Claus. My first real paid gig as Santa was for Microsoft. They were providing free photos with Santa as a way to demo a software program. People loved it… and come to find out I enjoyed it too.

Before long I had people asking me if I could make appearances at their home or office parties. I said “Sure, I’d love to,” and I did love it. I had a great time and not only did people pay, very often they even tipped.

So, the money was starting to come in… and I was feeling better about getting paid to ‘be’ Santa but there was a hole of sorts. My ‘community service’ had turned into a vocation and while I felt good about what I was doing and the joy I was bringing as Santa, I needed a way to contribute, to give-back.

I found that I could do some Santa appearances for not-for-profits and fill this void… perfect! 

5. Do your bucket list. As I my idea transitioned into a reality, a ‘retirement business’, I started to make a bucket-list of things that I wanted to do. Things that I thought were a stretch, but with some effort and perhaps some luck, within reach.

My list included things like appearing as Santa on TV shows, in commercials and

Santa Ed with Will Ferrell & Mark Wahlberg

in movies… all of which I have now done.

I keep adding to the list and remarkably I do seem to keep checking things off.

Is becoming an ‘Encore Entrepreneur’ right for you? If you’re in your 50’s or 60’s and trying to get a handle on what the future looks like… start with considering these 5 items. Take the time to listen to your inner self. Allow yourself to be guided by a soul-quest, a passion.

Remember to craft some ‘empowering questions’, questions that may allow you to find ways to do things, ways that are simply not visible at first glance.

Once you start seeing your way, start doing things. It’s essential that you go from idea to action. Take classes, offer a product or service for sale… most importantly… enjoy the process.

As your ‘retirement business’ begins to take shape marketing will be the single most important skill you will need to implement. By developing efficient marketing systems that reliably produce a steady stream of profitable customers you free up time to do more of what you enjoy.

Robin Ryan, if you should read this I want you to know that I love your book ‘Retirement Reinvention’ and as I expressed above I’ve lived it, at least parts of it. Thank you for identifying these ‘steps’ and expressing them so well.

Ed Taylor is an Encore Business expert devoted to helping those 50 & better build successful retirement businesses that they love. Get tips to create and build your retirement business at-




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