Illustrations by the author. Contact him for prints.

What I ask myself before I decide to quit

If someone were to ask me what words I’d use to describe working for myself, many would come to mind…

Stressful

Frustrating

Unstable

Scary

Draining (mentally and of cash)

Of course, these are not words and emotions that are in play constantly, and they are rarer for me now, but it hasn’t always been sunshine and daffodils.

Many times before, I’ve thought about stopping my own thing and working for someone else so that that life can be more secure.

It would be so nice just to be able to wake up one day; to not be confused; to not feel alone and weird and stupid, and to just have someone else tell me what to do for once.

But then I stop. I figure out a way to carry on with purpose and passion.

It is finding solutions to the following kinds of questions that help me find my way again…

Have I really run out of every option to make this work?

Could I do this if my life depended on it…if a gun was put to my head to make it work?

Is what I do (and can potentially give) pointless, or is it contributing value to the world?

Is it improving the lives of others in some way?

What might be the ONE thing that, if I were to push myself hard to get right, would solve most of my current problems?

Put another way: What is the ONE thing I am HIDING from that I secretly know would allow me to make my venture WORK if I applied myself in that area?

What aspect of my character might I be failing to nurture to full potential?

And… How can I develop that part of me — starting TODAY — in the knowledge that I MUST now make this work?

More questions to consider…

Is it more secure to have a single employer who could pull the plug at any moment, OR is it less risky to work with a variety of clients and customers (even if it requires more energy to maintain such clients)?*

*Read Antifragile.

If working for myself is isolating, what tiny step can I make this week to be with the right people?

If I cold emailed 100 contacts tomorrow, could this open up some opportunities?

If I had to do whatever it took to find a paid project or job for my business within seven days, could I do that?

If I secured one freelance job this week, whether tiny or large, would I be more motivated?

Might I be shutting myself off from certain opportunities because I feel that I am ‘above’ them?

If you’re struggling, no paid work is too small, unrewarding or meaningless — your priority now is to get your priorities right.

If I was able to make the above happen just once, could I do it again — and again, and again?

Might it be that my circumstances are NOT the problem, but that really it is my lack of commitment to ACTION?

If I decide to find employed work, will that decision have been out of reacting (victim mentality because I’m scared) or creating (the right move because I’m taking responsibility and acting courageously)?

Did I do the very best I could have done over the last six months to get the world to know about me and my work so that my business was at least sustainable?

Might it be that I am avoiding being ‘vulnerable’ in showing myself because I fear rejection … or is it that my work is so bad that not one of millions of prospects would want to work with me?

Would I find running my own business fulfilling in the long term, or would I prefer to help someone else grow theirs? If it’s the former, why leave it until later?

Ponder these questions, and see if you feel different about moving to employment. They have always proven to fire me up to make my projects work.

Note that running your own enterprise is not for everyone.

Working for someone else in a more structured environment for a while as I have done for shorter stints, can be a valuable thing, and this will depend on where you are in your career and on your responses to these questions.

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Originally published at www.redlemonclub.com on August 11, 2017.