CIO In Transition (Part Two) – I Need More Stuff in My Bucket!


July 1st was my three-month anniversary as a CIO in transition.  My how time flies when you are having fun.  I’m not being sarcastic at all.  These past three months have flown by as I ramp up into a new phase of my career that is completely entrepreneurial in nature.  It’s interesting that my last day in the office was April Fool’s Day, and my three-month anniversary fell on Independence Day weekend.  Hmmm.

I have always maintained a bucket list of things that I want to accomplish in my life and career (being the type A personality that I am.)  I was thinking about my list the other day, and I realized that I’m going to need more “stuff” to refresh the items that are getting done.  Here is the progress to my list:

Diana’s Bucket List Status Note To Self
Start a business √ √ I have started two businesses!  It’s like potato chips.  You can’t just have one.  My brother and I started our dream company, and I started one for consulting.
Independently consult I always thought that consulting would be fun, and it is. This part of my transition has ramped up quickly, and I can’t remember why I didn’t do this sooner.
Buy a vacation home abroad It seems like an elusive dream to most of us, but it is possible.  My husband and I close on our condo in Southern Mexico in late July.
Teach I mentioned this in my previous post, but it is a reality drawing near now.  I start teaching a class at a local university at the end of August.

This is a lot of balls to juggle at the same time, but I enjoy the different priorities that I have to focus on each day to keep all of the balls in the air.  I have dropped one a few times, but, as long as I keep trying and learning, I’m happy with the trajectory of my journey.

There have been a few surprises for me as I move into business owner and entrepreneur.  Those that have already been doing this will probably laugh and say, “See?  Small business isn’t that easy!”  In any case, here are a few observations:

  • Time is the most precious asset! I only have me to do all of the things that I dream up.  Every deliverable or milestone requires my time, since there is no one to delegate to.  For the control freaks, this is a dream come true.  It is not beneath me to ask my husband to help me with a few things!  My eyes are bigger than my plate a lot of times, so I have to be careful about what I take on.  Everything sounds fun, but there just aren’t enough hours in the day.
  • I’m abusing my car… My car has become my office.  I have driven more miles in the last three months than I have in the last three years.  Unfortunately, just like my old office, my car is a little messy now.  Papers, food bags, cups, spare shoes, and a bunch of other stuff now fill my backseat.
  • The tax and accounting guy is my best friend. After always having a corporation to take care of all of that stuff, it was a rude awakening when I realized how much there is to worry about that has nothing to do with the actual business.  I knew of these things, but I will now always respect my accounting and tax professionals for the innumerable details they take care of so the rest of us can focus on the reason why we created a business in the first place.
  • There is not enough time to learn and fail at everything there is to know. As a current client is fond of saying, “There is no way a small business owner has the time or resources to figure everything out by themselves.”   I’m grateful for all of the others that have gone before me on this journey!  I have been tapping into everyone I know that has a small business to understand all of the complexities.
  • I am my own master. At first, I tried to have a routine like I did in corporate life.  That really didn’t work for many reasons.  Mainly, a good idea or the solution to a problem comes to me at the oddest moments like when I’m shopping at the mall in the middle of the day.  I love the flexibility to creatively worry about my business problems when it is natural rather than on a fixed schedule.  I also like that I can shop or do other things during the day-time. No lines!
  • It’s a marathon not a race. Vision is a funny thing.  I can see what could be so clearly, but it takes time and patience to get there.  Well, I’m not patient, and, as I mentioned, time is precious these days.  Learning to be okay with daily successes and learnings is difficult, but I’m sure I’ll get the hang of it.

Thank goodness I thrive on change.  Every day is different and completely up to me to get through it.  Taking risks and going for it are in my DNA, so I’m thrilled to be able to call myself an entrepreneur and small business owner now.  I’m happy with what I have become so far in this journey.

I know at least one thing that will be added to my bucket list.  That is to stop calling myself a “CIO in transition!”  I was a CIO, but that is not who I am.  Who I am is more complex, more entrepreneurial, more altruistic, and way more fun than what a title can try to describe!


2 thoughts on “CIO In Transition (Part Two) – I Need More Stuff in My Bucket!

  1. Diana, sounds like you are having a great time in your new adventure. Jo and I wish you the best and may all your dreams come true.

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