The Glorification of Entrepreneurship

It seems like everyone these days claims to be an entrepreneur.  And if you aren't an entrepreneur, you're daydreaming about becoming one or a free-lancer or a business owner of some sort.  I don't know if it's my environment (Living in the Boulder area which basically the Bay area of the Mountains: startup central) or the fact that I've been listening to and reading lots of personal development podcasts and books lately, but the sentiment seems to be everywhere.  The entrepreneurs are sending their pity to those poor blokes who are sitting at a desk all day and urging us to come join them in the magical world of self-employment.  And the ones that are sitting at a desk are longing for "freedom."

My purpose in writing this is not to poo poo on entrepreneurship, free-lancers/self employed peeps (and let's get this straight once and for all, there is a difference).  I myself daydreamed about leaving my corporate job for something more.  I now supplement the family income with a photography business and it's amazing. No.  My intention is to bring about a different conversation.  

1) To talk about some misconceptions about being self-employed and/or an entrepreneur
2) To talk about WHY we find ourselves dissatisfied and longing for entrepreneurship
3) To discuss whether or not there is a better way to address the discontentment

So let's address the misconceptions.  I do not consider myself an entrepreneur.  People are misusing that world all over the place, and to be honest it makes me crazier than a betsy bug.  To me, an entrepreneur is someone who is creating something new in the world; systems and ways of reaching the world that are bigger than themselves.  People who make money while they sleep.  I consider myself a self employed free-lancer.   I trade my time, skill and expertise for money.  So although I wouldn't fit perfectly into the entrepreneurial category, the misconceptions can be the same:

If you are an entrepreneur you will make MORE MONEY and have MORE TIME.

I think this is a big time misconception.  If anything it's backwards.  As a freelancer, I can say that that yes I have more control over my time. But I don't know that any self employed person that is putting food on the table for their family would tell you they have more time.  It may be liberating to have autonomy and more choice in how you spend your time when you are working, but more time?  Not necessarily true.  I think about my father in law who has always been self employed.  For years he ran a restaurant and catering business. For a few years there, his daughter (my sis in law) called the kitchen "daddy's house."   I think about all the gym owners I know who are sometimes up at 4 AM to open the gym.  Most of them wouldn't have it any other way, but the burden is on them to keep things running and pick up the slack when someone is sick or someone quits, or s*&$ hits the fan when clients are upset.  I think about myself.  While it's amazing being able to be the primary caregiver  and chaeffer to our kids, I find myself up late editing photos or trying not to feel bad about planting my kiddos in front of a show for a while so I can do my book keeping.

Then there's the money part.  Ha.  Hahahaha.  I thought once I became a photographer, everything check I received would be straight profit.  Ha. Hahahaha.  What I so naively didn't realize off the bat is that....

 I had to have insurance.

And pay taxes.

And purchase systems to make everything run smoothly.

And buy more equipment.

And pay for classes to keep me fresh and skilled.

Etc, etc, etc.

Taking the leap from the corporate world to self employment is so scary.  It's not easy to walk away from the comfort of a paycheck that comes every two weeks to a world where you might not to get to write yourself a paycheck for months...or even years.

In the beginning a lot of times it means being the salesperson, the designer, the book keeper, the administrator, the visionary and the executer.  It means no guaranteed pay check.  It means, and this is the BIG one, stepping out of the daydream you've created and into the reality of it.

So what's the real issue here?

When we catch ourselves daydreaming about entrepreneurship (whatever that means to you) I think we'll do ourselves a huge favor if we ask ourselves...why?  Why is this so important to me?  Why do I want this so badly?

And answer honestly.

Because the truth is.  It's a hard road.  I think the real conversation we need to be having is are we willing to hustle for LESS time and LESS money in the beginning (and maybe forever)?

For some of us the answer is YES.  But for some of us, I think we'd be much better served to fight our demons and deal with our discontentment head from within rather than thinking a change of circumstances will fix everything.



This post has been brewing in me for a while now, but this is what inspired me to finally write it.  I'm part of a large, but private group on social media.  It's a group of entrepreneurs, free-lancers, and self employed folks.  Some of them are doing their thing full time, but some of them are side hustlers with big dreams.  The other day I saw this photo:

And this caption:

This is my desk. I sit here for 35 hours a week, next to a chap who could put Karl Pilkington to shame with his morose moaning (it is quite funny actually, but bloody negative) and I work in an industry I've been in for 10 years. Boring. 

I yearn to be that entrepreneur posting up my amazing home work station with geometric wall art, fish tanks, mothball free cats, bonsai trees and fancy notepads and colourful pens. Instead I'm here using communal toilets.

So here's what I do. I pretend I'm in a cafe, with a brand new Apple Mac in rose gold and the chatter around me is strangers meeting over a latte. I imagine having my gym bag at my feet to catch that 2pm spin class before the school run. I imagine having the feeling of satisfaction right deep in the core of me of having broken out of the mould and made a business from nothing. I imagine having that Michael Kors bangle clanging away on my laptop whilst I type messages to my followers. I imagine being so far from where I am, but also thankful that there is no rush. 







Please don't misunderstand me.  I'm not attempting to squash this person's dreams.  I think it's good to have a clear vision of what you want for your life.  I have it and I think everyone should.  I don't know her heart, her day-to -day, or her battles.  This is only one picture, one caption, one moment. But it really bothered me.  I had a visceral reaction when I saw it, and I mulled over it for several days trying to figure out why.  Most people left comments like "rock on!"  "You go girl"...and "you painted a perfect vision of what I want my reality to be as well."

It's because it suggests that sitting at a desk is not inspiring.  That it is lowly.  That it is sad.  That somehow, these circumstances are responsible for a dream that has not yet blossomed.  It's negative.  I've noticed that in my generation, there seems to be a glorification of entrepreneurship and a bastardization of the traditional 8-5 job.

I think it would be interesting to interview a bunch of corporate cogs turned entrepreneurs to see what their struggles have been once they took the leap.  Was is worth it?  What resistance did they face?  Did making the change make them happier?

My guess is that the answers would be widely varied.  I think some would say they are living the dream, but some would say it's not all it's cracked up to be.

I guess my point is this.

If you find yourself jealous of all us free lancers or longing for that entrepreneurial life, take some time to figure out what your values are as they relate to your career.  And then apply them to your current situation.  Because if you don't?  Chances are high that you will continue to feel disconnect and dissatisfaction even if your situation changes.  I think this concept could be applied to numerous situations career wise and elsewhere.

If I could only get that promotion, then I'll be happy.

I'll be successful when I build that best selling app.

I'm in prison working this 8-5

If I could only design what I WANT then I'll be happy.

Rather than banking on happiness, success, and contentment in your job coming from a change in circumstances, hit it head on.  Think about why it's so important for you to change your situation and figure out some things you can do to change your internal dialogue and actions in the present situation.

I'll use myself as an example.  For me, two of the biggest joys and motivators for me in life and in work is when I feel like I'm helping people connect with something or someone and when I can be creative, and when I can organize something.   So back in the day when I was in corporate training, I longed to be at home with my kids working some sort of part time gig doing just that.  Teaching accountants how to log an expense? Who cares about that?  Teaching a new hire the corporate policies and procedures?  Snooze.  But finally I realized...you know what?  Maybe this isn't the ideal job I'd design for myself, but you know what?  I can help people do their jobs better.  I can make a new hire feel more comfortable in a brand new environment.  I can design my own curriculum for goodness sakes.  Once I made that shift, I was so much happier and you know what?  Opening my mind like that, making a difference, and putting out positive energy helped me succeed in my job and ultimately paved the way for me to eventually make a change.

To I'd love to hear from you.

Do you struggle with this?

Are any of you entrepreneurs, free-lancers, business owners who have dealt with the post-honeymoon period of entrepreneurship?  How did you push forward?

Have any of you left the corporate world to start your business only to return?

Has anyone made the move to start their own business and found complete satisfaction?  What was your experience?

I love this conversation and I would love to hear your thoughts.