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When is it Time to Start a Creative Career?

It occurred to me that there may be loads of people out there who have been cooped up in their homes now for six weeks or so who are now considering a change.  I know there are gobs of folks who have lost their jobs, and who may not have employment to return to at the end of this journey, and that’s awful.  There are others who are small business people who literally won’t be able to rebound and reopen their businesses again.  That sucks too.  And there are still others who may be making some life-altering decisions about their values, how they want to spend their finite years on Earth, or who are wondering why they’re trading money for time. 

I haven’t seen any data coming through as of yet.  I think most people are still in shock, but this pandemic appears to me to be significant enough to warrant many people reconsidering their values and their lifestyles.   They may be enjoying working from home.  They may be reconnecting with their spouses and children, and seeing the difference being together can make.  People may be sensing that the amount of technology at their fingertips makes a 9 to 5 grind, with hours of commuting time, rather senseless.  Are we on the precipice of something pretty new and transformative?

When Bogdan and I had a significant change in our lives, that’s when we decided to go full-time into the freelance creative world.  We were working in Russia, and is typical for those kinds of expat jobs, it was time for us to move on to another assignment.  We had just purchased a home here in Texas, and my parents were starting to need a bit more support.  All of those elements collided, and we felt it was time for us to move home, start our dream business, and offer Mom and Dad the support they needed.  If you’re in that head space now, and you’re wondering if it’s the right time to make a change, let me give you a little advice based on my limited experience. 

If you are waiting for the “right” time to start out in a self-employed, freelance, creative career, it will never come.  There are always loads of really good reasons why you should wait.  You may feel you need to get a degree.  You may want to have more savings tucked away before you do anything drastic.  You may think your work isn’t good enough.  There are any number of great reasons why you should play it safe, and not make the plunge all at once.  You need to be sensible, responsible, and safe.

Then there are the stories of people who have a bad day at work, quit, and strike out on a new creative career with no planning, no preparations, and no safety net.  They feel that today is as good as any other, and if they don’t do something dramatic, they’ll never do anything at all.

I’m happy to say we fell somewhere in-between.  We had started a sole proprietorship back in 2010, and just kept it going in name for about five years before we decided to dive into the deep end of the pool.  That allowed us to play business for a while.  We could dabble into the organization and record keeping of it all, create a logo and a name, create resumes and websites, all while still enjoying a steady paycheck.  I remember my tax preparer asking dismissively; “What the hell is this business thing?  Get rid of it.”  I of course refused, though he was completely right.  We spent a year or so planning the new business.  We asked ourselves: Did we have enough talent? Could we make enough money?  How much would we actually need?  We wrote a business plan, a marketing plan, a budget, and explored who our dream customer would be.

Of course, once we decided to re-open the business as an LLC, most of that planning turned to be naive and inadequate to the task.  I still maintain that these were important exercises to go through, even if most had to be scrapped early on.  We opened the LLC in 2015, and have been completely self-employed ever since.  One of the first things I was told is that most small businesses don’t survive their first year, and may not be making a profit until even later.  What they don’t tell you is that when you complete that first year, they change 1 year into 3 years.  Once you hit that hurdle, the script changes again, as most businesses aren’t on their feet for the first 5 years.  We had savings, we kept paying our dues, and toward the end of our 5th year, a worldwide pandemic rocked the planet’s population and economy.  Well sh*t.  Difficulties aside, I have to say that we’ve never been as happy, or as productive as we have been over the past 5 years.

No one is going to be able to tell you what your comfort levels are, or to give any guarantees of success, particularly now.  The fact is that you will make the decision to strike out as a full-time creative when it makes sense to you, and not because you’re ready.  You’re never ready.  But the world around you has shaken the stability and sustainability of the livelihoods of so, so many people.  It would not surprise me to hear that there is a movement away from traditional employment and work life, to something more personal, something more flexible, and ultimately more rewarding.  Come on in guys, the water’s fine.

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