OFI 372: A Tale Of Two Entrepreneurs | Which Entrepreneur Do You Want To Be?


When it comes to entrepreneurship I find myself caught between the images of two different entrepreneurs.

As a kid an entrepreneur was a person with a vision and the passion to make that vision become reality.  The entrepreneur of my childhood would work 80-100 hours per week to make that vision come true.  And someday, somewhere in the future it would all come together and they would achieve success.

Today when I read about entrepreneurship it is all about lifestyle, morning rituals and pivoting.  The way that entrepreneurship is getting sold is based on the life you can have, not the money you can make. The wealth accumulation motive is still there, but from what I can tell it comes second to lifestyle.

The entrepreneur from my childhood still exists.  They still start restaurants and dry cleaning businesses.  And the whole family is still devoted to making the business succeed.  I don’t think they ever went away or ever will.  But today the lifestyle entrepreneur has emerged.  Both exist in a world that now offers more opportunities to start and succeed in business than ever before in history.


Since I began my entrepreneurial journey in about 2009 I have been reading about morning rituals.  In all honesty, I considered the whole concept to be just a fad that made people sound cool.  But as time went on I started interviewing more and more successful entrepreneurs that talked about having one of these routines.

I started to think that there might actually be something to this, so I am giving it a try.  For the last few weeks I have been “finding an hour” each morning to go on a walk.  All that really means is that I am getting up an hour earlier and hitting the road (or in my case the canal) for a walk well before the sun comes up.

So far I am discovering myriad benefits.  Just like everything else in entrepreneurship, you just cannot see all the benefits until you get out there and start doing it.  Here is a list of what I like about this:

Seeing The Stars: I love to see the stars in all their glory, but I rarely make this happen on purpose.  Usually, by the time that enough light fades away in the evening to give me a really good look at the stars I am crawling into bed or watching television with my daughter.  But on my morning walk the stars are vibrant and they are in a different position than I am used to seeing them.  This is really one of the top things I look forward to when I go to bed at night.

Hiding From Farmers: Now this begs for some explaining.  I say this mostly tongue in cheek….mostly.  As an aspiring farmer in my community I pay attention to what the social norms are in my peer group.  As far as I can tell recreational activities like long walks, jogging and bike riding are not one of those norms.  So, by walking at this time of day I am turning otherwise unproductive time into something beneficial, and I can pull it off without anyone being the wiser.

Fitness: I feel great when I am done with my walk, and I am wide awake.  The endorphin release from the exercise is just what I need to power me into the rest of my day.  And my belt seems to be a little looser.

Connecting To Old Ways: One of my favorite authors, Jerry Apps, writes all about farming in the 1930’s, 40’s and 50’s.  In one of my favorite stories he talks about a neighbor, who lived over a mile away, walking to their house on a snowy and windy day for a visit.  The farmer was dressed in a warm hat and a Mackinaw wool jacket to protect him from the weather.  On my walks, as I pass all my neighbor’s farms, I feel connected to that story and those simpler times.

Thinking: There is something about a peaceful walk when it is beautiful and quiet outside that really gets the mind going.  This works so well that now I am deferring thought on certain topics until I take my walk in the morning.  I know that I will really be able to devote myself to that one particular problem or concept during that time.  I do not listen to music or podcasts on this walk.  I just listen to the wind, to the dogs barking and the roosters crowing and let myself think.


My walk this morning really got me thinking about the two entrepreneurs I described at the beginning of this post.  There is no question that I chose entrepreneurship for the lifestyle.

Don’t get me wrong, I am not afraid to work.  As a matter of fact, when I first started I had no choice but to be that 80-100 hour per week entrepreneur.  I don’t think that any entrepreneur has a choice if they are going to transition from full-time career work to full-time entrepreneurship.  During that transition period you are going to be working your career job while you build your business into something that will allow you to quit the career.  You will be doing double duty during that time….which I did.

And, the lifestyle I was seeking was not one of leisure but one of farming.  So there is always plenty of work for me to do….if I want to.

What dawned on me today was the lifestyle that I have been able to achieve by making this transition.  My career life was one of odd schedules, long weeks, being called out in the middle of the night, conflict and stress.  Today, I am in complete control of my schedule and the future looks bright.

I am in a phase of life that has more to do with raising my daughter than it does with achieving my personal goals, financial or otherwise.  I have been a full-time entrepreneur since 2013.  For the last four years, while my daughter was in 2nd, 3rd, 4th and 5th grades I have put her on the school bus every morning and been there when she gets off.  I have been at all of her sporting events and I am home with her every night.  I have even coached her softball teams.

I am able to do all of this because of entrepreneurship, not in spite of it.  I have dreams of what I can achieve when she is off to college and working 50-80 hours weeks will not feel selfish.  But those can stay dreams for now.

The biggest benefit of entrepreneurship that I have realized since making the transition is what it allows me to do, and how it allows me to live.

Why are you choosing entrepreneurship?  How will it allow you to live?


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