Cartesian Merger

This week I helped one of my clients hire their first employee. The women they hired is a perfect match for the organization and I look forward to working with her. During her interview the new hire asked several questions about the work culture within the organization, her questions came out as more of a cautious inquiry - What days and times she need to work? If there were weeks when she worked less then her contract 20 hours was that ok, could she work more hours if needed other weeks?

Much to her surprise and pleasure when she had asked her questions my face lit up, I might even have giggled. I immediately told her to relax. What is important to the culture of this organization and to me is the work gets done with excellence, in a timely manner and that the people doing it love what they do.

I have file folders full of templates for work plans, paper and digital systems for project and time management which provide the architecture for working in a more organic and individualized fashion.

This management style plays to individual strengths - some of us work better in the early morning, some of us (ME!) crash hard at 3pm and need to get out and get some exercise before returning to work, others like to work in the evening, standing up at their desk, working with music or without. Thinking about the merger of work and life rather then the separation of work and life provides flexibility, creates a more productive work environment, encourages creativity and in the end the product, whatever that may be, is better for it.

Dennis Crowley the CEO of Four-Square was interviewed on Marketplace a few days ago and I love what he had to say about going to work, it is a feeling a share and the type of work environment I help my clients create.

Crowley said, "I never think of it as going to work everyday. It's just, hey this is where I go to do the stuff I like to do."

"I just want to work for myself" - Why the grass is sometimes greener

Recently a friend wrote me to ask how I make it work, referring to working for myself. He is justifiably frustrated by the dynamics in his work environment and looking for a way out. He is also a talented artist who would love to make a go at turning his part-time painting gigs into a full time venture. I hope he reads this - I think he has the talent and drive to make it happen.
His inquiry got me thinking about the challenges of working for yourself, the realities between the appealing bullet points of self-employment.

So here is what I have to say to anyone considering a shift to self employment...

Don't be so quick to only see green grass on the self-employed side of the fence. I love working for myself, it works for me, it supports the lifestyle I am excited about but here are drawbacks to consider and honest realities of dark side of self-employment...

-Success will require you to be the hardest boss you have ever worked for.

-Higher taxes.

-Wrestle with the fact you will never afford the kind of health insurance you had when you worked for a company...you will settle for basic coverage you pay too much for and family plans - forget about it

-No paid holidays, sick days or vacation. You take time off ...you don't make money.

-When you screw up there is no one to blame but yourself

-No IRA contributions

-Be prepared to work 2 + years before really making any money

-Realize that your business is YOU so it doesn't really ever get turned off (ie: trip to Peru...computer comes, emails are answered and that's vacation)

-When work is insane you don't get to run, play, visit with your spouse until the work is done

-If you don't have a spouse who is bought into the entirety of the plan above you will also contend with that

-Plan to spend less then you ever thought you would - dinners out, buying the smaller house, not buying a new car, holding off on major purchases until your business is stable.

The upside....

If you can handle the discipline required
If you can figure out the expenses of running a business
If you want flexibility
(read periods of intense work and then down time)
If the idea of kicking your own ass beats someone kicking it for you

.....you can do it.


It will be hard. You will get frustrated. There will be times you have no clue where the money is going to come from. You will have months where a day off means you don't have meetings but your read email before going for a run, answer a call while on it and check email again before bed.

If all of that is still agreeable. Find what you you love and go for it. If being my own boss has taught me anything it is that you don't have sit in a job you hate.