I mean the long view here, where I worry that I don’t have a clear enough plan for what will happen in the coming years of my life. Sure, there is security in following the same path that I’ve been on for the past 10 years, keep the routine going and try to ignore the sensation that I am repeating myself. I feel bored that I am solving the same problems that I did before, just using new words, the latest technology or adjusting for a younger attitude. I’m sure this is true for many middle aged people in the workforce who have enough experience in their particular industry to question if they are really innovating. Are we just trying to address the exact same business problems that we noticed ten or twenty years ago?

Maybe if you had actually solved them you wouldn’t have to keep trying.

But I did solve many of them. I can tell this is true because so many customers told me it was true, right? The key performance indicator is whether other people find value in the solutions I found to their problem. That does not always mean they find the results to their satisfaction for extended periods of times. They spend their own time thinking a lot about what they should be doing and so their problems take on new forms, which means the valuable answer I offered earlier becomes diluted by additional variables.

So, I rinse and repeat. I look at the issues facing the customer from today’s point of view. And I calculate a way to adjust my answers, to add features and functions to my solution. Or more often than I would care to admit, I decide the challenges facing that one particular customer have changed so radically than what they expressed previously that it is best to let them go. There is a life cycle to every business relationship; a beginning, middle and end. 

That is a free economy, dude. You can’t expect things to stay the same forever.

Wow. So now I am the old man that is stuck in his ways? I have another take on that. There is wisdom in having the maturity to know there comes a point when my ideas are no longer working for the other party. This happens when they bring me new ideas that I have not prepared responses for, so I tell them I need to think about that and get back to them, but never follow up. Or it happens when they tell me the original goals they brought to me in the first place have been replaced with objectives that I am not prepared to assist them with. I do not have the machinery, or the resources, or the expertise to marshal an offering that will convince them I am still the solution provider.

What happens when a business, or me as an individual, has matured enough for this pattern to be noticeable? Where do I spend my time? Historically this has propelled me to find a different niche to service. I look for a move that is horizontal perhaps, attaching myself to the same industry but addressing a fresh set of business issues using ideas and technology. I have also moved to completely original verticals. Drop whatever markets I spent a decade learning and sail into a brand new group of products, services and special interests.

Sounds like you bounce around a lot. Do you have an attention deficit disorder of some kind?

Good question. I look at a fair number of resumes of other people and a major red flag goes up when I see they have switched jobs every 12 to 18 months, and have they done that more than once or twice. When I ask them there is always an explanation for each jump but I always sense that after working with me for a year there will be yet another logical explanation why this individual will move on. So, given that sensation, I am ultra-sensitive to the possibility that I have myself moved around too much over the years. I have indeed held more positions than I have lived in decades, but that is not how I care to judge the experience in my case. For myself, the logical explanation, in hindsight, has been to call myself a serial entrepreneur. I start businesses and take them to a certain point in their life cycle. It is becoming clear to me now that the point at which I face a challenge is when the problem solving becomes a rinse and repeat cycle. At that point my skills as an entrepreneur shine less and my deficiencies as a manager bubble to the surface.

Oh my, is that what I mean? Is the point that managers rinse and repeat and entrepreneurs work with ideas and solving problems? 

That is a dim view of the art of management. There is considerable skills required to manage well.

No doubt! And what I am saying is the successful manager is the one who can rinse and repeat without feeling they are standing still. They can appreciate the nuance in the repetition and carefully make small adjustments in procedure and work flow in order to improve production, maximize time and mentor team members.

That’s falling forward.