This second of the Ten Steps to Starting a Business After 40 represents a personal challenge for me. In order to find out what you enjoy doing, you have to let yourself enjoy it first. And as much of an accomplishment as that might be, you may also have to accept that you can’t make money doing it.

Person lying in tree

This is a search-your-heart, not search-your-head, exercise that needs its proper time and space.

Rob Mulally

When Self Knowledge is Elusive or Worse, Unwelcome

This step may seem easy and obvious to most people. It’s not to me. It has always been difficult for me to admit to myself the things that I enjoy doing. And if those things don’t produce tangible results or benefits, then it becomes difficult for me to enjoy doing them without feeling guilty. I would say my sense of duty and its twin, my sense of obligation, are overdeveloped and frequently rob my experiences of enjoyment.

I attribute this, in part, to growing up in Massachusetts. I’m not joking. The Puritans’s landing place is a serious state with a history of fulfilling responsibilities very seriously. People here put themselves under a lot of pressure not only to succeed, but to succeed through conformity to very narrow standards. Standards that aren’t always kind to human beings. Or their diversity. That’s not an easy way to live.

I attribute it, in other part, to being born under the sign of Capricorn. I’ll save my astrology soapbox for another post. But aside from a certain seriousness to their dispositions, Capricorn natives are also very pragmatic. I have no doubt that the people who know me would not use that adjective to describe me (astrology will not be oversimplified), but internally, one of the first things I ask myself when confronted with new circumstances is not, “What do I want to do in this situation?” It’s, “What do I think it is possible to do in this situation?” In other words, I immediately assess my options through limitation.

This “heavy” approach tends to kill spontaneous enjoyment. It also tends to restrict the activities I will actively pursue or initiate to those that create some kind of practical (versus say, artistic or recreational) value for others or, more often still, to those that support value created by others. Given my particular past, it is easier and less problematic for me to put the ideas of others ahead of my own, to give others more credit than myself.

I’m not sure I always enjoy doing said activities in and of themselves; that is, given other options from which to choose, so much as that I can give myself permission to enjoy doing them since doing them is acceptable because they are worthwhile, as judged by others first and self second. (We won’t get even into the standards or whose by which “worthwhile” is to be measured.)

As Stephen Stills’s song says, “Love the one you’re with.” Only in this case, I would translate it as, “Love the thing you can (allow yourself to) do.”

I’m pretty confident I’m not alone in feeling this way. For some of us, identifying what we enjoy doing is a process fraught with discomfort and a certain amount of risk; i.e., the risk of disillusionment.

The Disillusionment of Necessity

Some of that risk and discomfort is mitigated with the knowledge that this step isn’t about taking time to find out what you enjoy doing in a vacuum or what you enjoy doing purely for recreational enjoyment or pleasure. This search is intended within the context of earning a living by starting a business.

That makes the stakes feel different to me. I suppose it can’t hurt to take a blue sky approach to analyzing what you would enjoy doing for a living. If the sky were the limit and you could monetize any activity you enjoy, what would that be? Maybe that opening would actually summon possibilities of greater flexibility and creativity than you would otherwise consider.

My personal feeling, however, is that if I’m going to eliminate impractical options later, I’d rather not consider them in the first place. Because identifying what you enjoy doing in this context must be tempered with the necessity of doing it day in and day out in a fair exchange for money, sometimes when you really don’t want to. Without taking necessity into consideration, how to be sure you can sustain doing what you enjoy doing over the long term? How can you commit to crafting and producing dependable, predictable results over time, if you’re relying upon inspiration that falters when enjoyment ceases?

Growing up, I had always thought I would be a teacher, as had been my paternal grandmother. But at 12 years old, I was bitten by the acting bug. I had done a school play in the sixth grade that I enjoyed very much. In eighth grade, I did so well in a short drama course that I was invited to play the role of Louis Leonowens in a local college production of Rogers and Hammerstein’s, The King and I. For an eighth grader to attain a role in a college production – including a live local television segment to promote it – felt like a miracle.

Thus began a lifelong love of theater and performance. From high school through college and beyond, I performed in straight plays, musicals, and revues. After Elaine and I were married – we had met in an acting class – we performed in straight plays, musicals, light opera, and community opera throughout our nine years in California and our six years in Maine.

All along, I thought I would one day perform for a living. I thought that’s what I wanted most to do in the world. Certainly, I would have said it was what I enjoyed to do most in the world. And if years aren’t an adequate measure of time taken, I don’t know what is.

But even after all those years of knowing how much I enjoyed it, I never made a living at it. What bothered me most was that, as far as I went with it in all those years – another subject for another day – I never even approached making a living at it.

What this has ultimately taught me is that not everything you enjoy doing will provide you with money, let alone serve as a solid basis for starting a business. Recognizing that and making peace with it may be necessary for you to move forward, as it has been for me. Granted, I was luckier than many because I was able to move forward riding the coattails of Elaine’s initiative to found first Dishes Delish and then Maturepreneurial. So here I am.

Lady with scallions

Maybe you can’t do what you love, but you can always love what you do.

paul morris

The Practice of Enjoyment

In his podcast episode, Henry Lopez says that the best advice he ever received was, “Enjoy the journey.”

This was hardly something he had done his whole career. As a serial entrepreneur, Henry started many businesses, but always with stress and angst. He could only let himself feel good and enjoy himself when he had achieved “some arbitrary mark of success, whatever that was.” It might be opening the doors to a new business or reaching a certain amount of revenue.

He states, “What I learned from advice from others is to enjoy more the process and understand that what I create – a new business, a new concept, or a new product – all I can do is put my best into it. All I can do is have it represent the best of me and put as much effort and care into it as possible. And then, it is out of my control as to what the public does with it.”

He has been practicing this mindset with focus and consciousness ever since.

Henry makes the valuable distinction between setting goals, which are necessary if arbitrary, for giving us direction and focus, and maintaining our perspective toward fulfilling them. Because we are so conditioned that nothing is good enough until we get to some mark of success, whatever it is, success has to become a moving target in order to maintain that condition. We accomplish our goals and immediately set new ones with which to harry ourselves.

More often than we do, we could stop and appreciate, “Isn’t it great that I have this opportunity? That I get to do this [insert your business here]?” In fact, doing so is important.

Henry also suggests that enjoyment is a good test of whether or not we’re cut out to be entrepreneurs in the first place: “If you don’t enjoy the process of creating, then I’d have to question what it is that you really enjoy doing.”

So while Step Two is about taking the time to identify which journey you would most enjoy when starting your business, it would be wise to expect that practicing that enjoyment will sometimes require your conscious intention.

Photos sourced from

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