Step Two: Take the time to identify what you enjoy doing

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

Step One: Take the time to identify what you’re good at

Taking the time to find out what you’re good at is the first step in our ten-step series How to Start a Business After 40. It may be easier than it appears for some of us; harder for others. We’ll delve into each of the other nine steps in separate posts.

Men running hurdles

Do you know what you’re good at?

For many of us, by the time we turn 40 or older, we’ve already been doing what we’re good at. In fact, we could do it in our sleep. If we were lucky enough or self-aware enough to have entered and advanced our careers by playing upon our strengths, then we’re pretty confident that we know what they are. If you fit this description, please hold.

If, on the other hand, and figuratively speaking, we have been doing what we’re good at “in our sleep,” then we may not be aware that we’re good at it because we don’t have the objective perspective to see ourselves doing it well. This kind of oversight is not trivial or uncommon.

For those of us who have not been so lucky or so self-aware to have played to our strengths before now, that may be because we pursued fields we thought we were interested in but that ultimately never quite fulfilled us or to which we really weren’t suited by temperament. Maybe we’d already invested years and thousands of dollars in a course of study we were reluctant to abandon. Or maybe it just took time and experience to recognize a bad fit.

For others of us, perhaps we have played to our strengths, but we’re bored. Been there, done that and now, after 40, there’s an opening, an opportunity to reevaluate or to embark upon a second or third chapter in our lives, and we want to do something different – something that is personally fulfilling versus just professionally remunerative – what then?

Maybe we’ve never stopped to consider what we’re good at because we never had the time or the mental bandwidth to do so. Life just swept us along with demands and obligations that came early and that we’ve been busy fulfilling during our 20s and 30s. Or maybe we’ve always taken the path of least resistance and simply did whatever was the easiest or most expedient thing to do in order to make a living or pay our way.

Do you know how you know?

Whatever our backgrounds and wherever we stand today, when we relate this first step to our personal experiences what we may not fully appreciate is the recommendation to “take the time”. Taking that time formally or informally or recognizing how and when it was already taken, consciously or unconsciously, is essential when it comes to the express purpose of starting a business or entrepreneurial venture. It’s a process of taking stock of your assets, your knowledge and your strengths that can result in much more than simply knowing what you’re good at. It can lead you to a successful business proposition.

Variations on this process and its results have been described by more than a few of Elaine’s podcast guests. The benefits and advantages of such a process are also strongly suggested in several authoritative books recommended by many people who have enjoyed success in business, including Michael Gerber’s The E-Myth Revisited and Napoleon Hill’s Think and Grow Rich.

Hill poses questions for self-examination all throughout his book, but towards the end, in Chapter 15, he presents a comprehensive list of around 75 questions the reader should ask himself, stating, “At least one day is necessary for the analysis and the answering of the entire list.” Although the book was published in 1937, this strikes me as a novel concept. When was the last time you spent a day with yourself, analyzing yourself and how well you know yourself? In my case, the answer to that question would be, never!

In Gerber’s book, which offers eminently practical and actionable advice and direction on many entrepreneurial topics, he becomes almost mystical in discussing what being an entrepreneur can do for us personally and the opportunity it offers to connect to and manifest our earliest childhood desires and intentions; the dreams we had that, hopefully, have had some influence upon and connection to what we’re good at now and how we express this skills professionally. The role of Technician that he discusses so thoroughly embodies these elements of personal expertise and highly developed skill sets.

An example of one discovery process

Johannah Barton, founder and principal of Confetti Design, a web design firm in Australia, describes in her podcast interview a very modern and original approach to this idea of identifying what we’re good at. She characterizes it as kind of a modern business plan. Before she founded Confetti Design, she took herself through what she calls a discovery process that had three components. I’m only going to mention the first one here. I’ll save the other two for future posts that delve into other steps to starting a business after 40.

In the first step, Johannah sat down and wrote out everything she had ever done in her working life – all the things she loved about them and all the things she didn’t love – and what she learned from those experiences. She then sent off to a small group of friends and family a list of her strengths and the question, “When you think of me and of asking me to do something – just me – what would it be that you would ask me to do?” She then collated the external feedback with her internal insights to create a sort of visual landscape of who she was and what she had to offer that was unique.

As I said, there is more to Johannah’s process and we’ll discuss the other components in a future post. In the meantime, I recommend you listen to her interview to hear what she did in her own words. The point I want to make now is that Johannah found this discovery process so valuable to her own personal success and focus, that she turned it into a business offering for her clients. This process is also something that she repeats or revisits on a regular basis at different times in her business cycles, because not only does it give her confidence, it gives her proper actions to take when she turns to marketing: where to go to reach her audience, what tone and language to use, and how to position herself and her business.

For Johannah, the self discovery process was a critical first step in determining her unique value proposition, as it will be for you in determining yours.

Man shaping clay on potter's wheel
Quino Al

A billion other discovery processes

Johannah’s is just one process. Obviously, there are many other ways to achieve self knowledge; probably as many as there are selves to discover. Many entrepreneurs simply repurpose what they’ve done during their professional careers into a business of their own, in which case the business becomes an effortless and natural extension of what they already know they’re good at. Others may discover an entirely new application for what they’re good at; one that breathes fresh and enthusiastic purpose into their lives. Others may have to take stock more consciously. Their self discovery and self evaluation may need to be focused and intentional, as Johannah’s is and as some business gurus recommend that it be.

Still other people’s processes may be or have been haphazard or incidental to their efforts to earn a living and put food on the table. In this case, their strengths and abilities may be something they become aware of gradually, over time. These assets may have been ripe for discovery, but overlooked or not yet fully appreciated, waiting for the right time or awareness to reveal themselves. But chances are they won’t reveal themselves, or we won’t recognize them when they do, unless we go looking for them.

Whichever scenario applies to you and how you take stock of your strengths, your assets, and your skills – formally or informally – taking the time to find out what your good at is a necessary first step to starting a successful business.

Related podcast content

(hyperlinks don’t go to timestamps)

Resources for self-awareness

StrengthsFinder 2.0
The Myers & Briggs Foundation
Quiet: The Power of Introverts in a World That Can’t Stop Talking

Photos sourced from

Introducing The MP Blog: Leanings, Gleanings and Ruminations

Our first official, but second chronological, post in which Christopher introduces the Maturepreneurial blog and ruminates on managing the admittedly self-imposed pressure to get things done.

Monkey sitting and thinking

The better part of our natures. We love monkeys.

Elizaveta Korabelnikova

Dear Reader, I’m Christopher. In future, I won’t make that distinction. You can see it in the byline anyway. But I thought I should observe the formality here and now, since this is my first and official introduction to the world as one of the voices of Maturepreneurial. Elaine had the idea for the business, did all the research, and put all of the structures in place to create the business, including the nuts and bolts of this website, of which I am very proud. I only had to provide various kinds of support, but primarily administrative and editorial support. I do the same for the Dishes Delish food blog, but I haven’t come out there publicly yet either. Elaine has encouraged me to put my picture and bio on both sites, but I’ve been slow to execute.

Or fast to execute. It’s harder to tell as I get older, or perhaps I should say, as I live longer, whether I’m behind or ahead, since there is so much opportunity for spending my discretionary time and energy. Add to that abundance the limitations of a full-time job and then all of the other activities that are such a necessary part of living but feel, mentally at least, like bolt-ons to my “real life” – the main event, the inner thread that I track in gold and consider the expression and purpose my most genuine self – and circumstances become ripe for disorientation.

I suppose it’s really a case of glass half full or half empty, depending upon my view of my goals at the particular moment I’m taking measure of my progress, that determines whether I truly am behind or ahead. In any case, this is all my long-winded way (get used to it) of saying, that I haven’t done that yet. And in case you forgot my referent, which was some 175-178 words ago, depending upon whether you consider hyphenated words singles or doubles, I’m talking about not having put up on either of our websites – or – my picture and bio. Hence this formal introduction.

I will get to the picture and bio in due course. I promise (me). In the meantime, I remind myself that it’s only Elaine and me right now, that we’re getting so much done on a daily basis for both websites, and that I have to be realistic about how much I can accomplish and, more essentially to my feeling behind, how quickly I can accomplish it. I used to measure effective execution of my goals in minutes. (Minutes! Ponder that insanity for a moment!) Then I came to measure it in hours. And then days, which are still the outside limit to how long I’ll take to reply to emails, for example, without feeling like a lazy, anti-social slacker.

It took me years – literally until I was in my 40s – to begin to permit and/or admit the measurement of some forms of execution in weeks. That was a stretch I never thought I would exceed. Now, at 57, I’ve recently shocked myself by actually recognizing, contemplating, determining – in case it’s not clear, I’m not sure which word best suits – a lead time until goal completion of years. Yes, I used the word years. As in one or two, mind you. But still. Years. Having come this far, I can now imagine accommodating – nay anticipating – a duration of decades to complete some tasks or achieve some goals. This should qualify me to pass for the accomplishment of at least some level of maturity, shouldn’t it?

To the extent that it does, I guess I truly have become a maturepreneur.

So, I set my goals internally and somewhat informally; i.e., without hard deadlines but more an intuitive sense of an acceptable length of time until completion, and then I do as much as I can to advance them. I do this in the context of fulfilling my other obligations, including my obligations to myself: taking care of my body with proper eating, exercise and rest, pursuing and nurturing my passion for music, and finding some time to relax and enjoy myself. It ain’t easy to do all that!! It’s even harder to do all that and feel like I’m getting ahead.

But, the truth is, I am getting ahead. I’m farther along than I was yesterday, certainly than I was a week ago, and I urge myself to have the faith to believe that I’m getting where I want to go. In fact, based on my own personal history, it’s a lot easier for me to believe that I’m going to get to where I want to go than that I will enjoy the journey that brings me there. And because that’s the case, I’m trying to be more vigilant about taking my time than about staying engaged in fulfilling my objectives.

Guy with feet on wall on beach

What “taking one’s time” might look like.

Elena Saharova

Welcome to our blog. Here we plan to post leanings (our opinions and/or commentary), gleanings (what we’ve learned or would like to distill for our readership from what others have said, sometimes literally, in the case of our podcast guests) and ruminations (which would be, well, like this post, for example).

Constructive, respectful, and authentic comments welcome.

Blog post photos will virtually always come from, a website of free photographs from all over the world that we highly recommend you visit and peruse. The photos are amazing. 

How to Start a Business After 40

Here are ten essential steps for starting a business after you’re 40 years older, wiser, and saner; a road map for the journey to your future.

Bike under work sign
Javier Calvo

Ten essential steps to starting a business after 40 years old

Life looks different after you turn 40. And hopefully better. If you’ve ever wanted to enjoy the independence and fulfillment that comes from starting, owning, and running your own business, here are the ten steps you need to take.

  1. Take the time to identify what you’re good at. Be clear and specific. Enlist the help of others you trust.
  2. Take the time to identify what you enjoy doing. Be honest with yourself.
  3. Look around to identify a need among a particular group or class of people, activities, businesses or entities. Be thorough in your research.
  4. Determine where lies the intersection between what you’re good at, what you enjoy, and a product or service you could provide to fill the need above. Get creative here.
  5. Create an avatar of your specific customers from Step 3. Be detailed and specific. It will focus your efforts later.
  6. Create a plan or platform (e.g., a website or other online presence or brick and mortar location) for reaching those customers and marketing your product/service to them. Be detailed but flexible. You may need to change course (see Step 9).
  7. Find a mentor you can trust and work with or learn from to support your efforts; whether it be someone close to you, a professional for hire, a published author, a community of like-minded people, or some combination of the above. Keep learning.
  8. Launch your business and execute on your plan as consistently as possible.
  9. Correct your course as you execute, learn, and identify knowledge or activity gaps you must fill. Wise up, don’t give up!
  10. Patiently stay the course to profitability. Revisit this list regularly to refocus and refine your efforts.

Not saying it’s easy. Each step comes with challenges and rewards. But follow this blueprint with persistence and perseverance and you will succeed. It’s never too late.

Optional follow up: Help others to do what you’ve done!