Giving Myself Permission



Photo c/o Tutti del Monte

For five years, I worked a Monday through Friday 9-6 with a lunch break.  Growing up an athlete where I lived, breathed and ate on the tennis court, and later coached this was complete torture.  To be in an office by myself for 40 hours a week was a test of my will.  But I knew in order to get to where I wanted to be not only was it necessary; it was actually a blessing.

The first thing I did when I got into the office each day was turn on the computer, printers, and scanners, check the calendar to see if there were any meetings or events that day.  Then I would take out my yellow pad of paper with blue lines on it and write my daily to-do list.  During busy season I would easily fill out two full pages of things to-do and then add-on throughout the day.  But during our winter slow season it was a different story.

I remember it being early January one year, and we were slow(wwwww).  I came into the office Monday morning, turned everything on, checked the calendar to see no appointments for that day, week, and even the next few weeks.  Then I grabbed my pad of paper and pen and just sat there for  a few minutes drumming my pen on the edge of my pad of paper racking my brain:  What in the world am I going to do (not just today), but for this whole month!  What is the point for me being here this week.  It’s all pointless busy work at this point.

I was fine packing my stuff up and calling a spaid a spaid and saying ‘hey boss see you next month, I’m going to the beach’.  But I knew that wouldn’t sit well with him.  After staring blankly for what seemed like an hour I finally came up with two things for me to do that month day:

  • Organize my email into folders with labels and tabs.
  • Clean and organize the supply closet.

You can imagine how inspired I was.  How in the hell was I going to make that into a whole 8 hour work day, let alone what was I going to do for the next 4 weeks?  Surely I was going to die from boredom or the fumes of all-purpose cleaner as I cleaned the closet for the 29th time.  But alas I did not.  I made it through.  I found things to do, and I did not die of boredom.

What I remember about that day, and days like it was this though:

When I run my own business I want to work hard and efficiently.  None of this 60 hour work week business.  And on days that were slow I wanted to give myself permission to enjoy those moments.  Pack up and go to the beach on a Monday for a few hours.  Go to a midday workout class.  Have a long lunch.  Because inevitably there will be a time a few months down the road when we’re drowning in work and 12 hours days seem as normal as breathing and I’ll have wished I took some time off in the dull days of winter or spring.  The calm before the storm.


Now three years into my running my own business now I’ve learned a thing or two.  For starters:  I’m a harder boss on myself than any other person I have ever worked for. I can just be straight mean to my employee (me).  Instead of letting her go out with friends I boss her around, and make her work through the night just to hit a self-imposed deadline.  Anyone with me?

I’ve also learned that when it’s your own the amount of ownership you feel over every aspect of your business is infinitely more than when you are working for someone else.  I’m always thinking of things to do, portfolios to update, hard drives to triple back up, meetings to set up, articles to write, people to reach out to.  It’s been three years, and I still am looking for that ‘off’ switch that seemed so readily available to me when I worked for someone else.

Giving myself permission as a business owner to enjoy the perks of running my own business is a hard thing to do.  It’s an actual muscle that needs to be strengthened, and is actually a good thing to have in your ‘arsenal’.   I try to remind myself of what I wanted when I started my own business.  What type of lifestyle I was looking for.   And enjoying beautiful middays in the park, and taking trips and working really hard in between was what I wanted.

This week giving myself permission looked like taking a few hours off to ride bikes with my best friend in Brooklyn.  After I got over the initial ‘guilt’ of not working I enjoyed myself so much, and was able to get back to the office and work really hard later that day.


If you’re a business owner or freelancer like me, how can you give yourself permission to enjoy your lifestyle more?  Maybe it’s just taking a 15 minute break, and walking to get an iced tea or maybe it’s finding an airbnb in Paris for an off-month to work and live remotely.  Or maybe you struggle with balance or giving yourself permission.

Whatever it is, I’d love to hear it.



1 comment on “Giving Myself Permission”

  1. I am hoping to go into business for myself in the next two years, and this is something that I fear all the time! Currently I work for a big corporation in digital marketing, and I have an online fitness coaching business as a side gig. I find myself working 24/7. Never able to turn that off switch off and relax. I think my problem is that I am trying to prove to myself and everyone watching that I can do it all, and I am not a failure. My ideal lifestyle when I go into business for myself would be to enjoy those days when I can go out for lunch or go to a 30min fitness class during my lunch hour. I am very tough on myself so I don’t see me giving myself permission. Great Article!

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