159. To Quit, Or Not To Quit

How do you know if you should quit or not? Sometimes quitting is in fact, the wise and right option. Freelancing isn't easy. It takes courage and tenacity to push through. It starts out being fun, like a great adventure, especially when you land your first couple of clients and get paid for the projects. But when obstacles and opposition show up, what will you choose?
Way back when I was just starting out on my freelance journey, there was so much I didn’t understand about how to make it work.

There were things I was sure of: I didn’t want to work for someone else, I wanted to earn enough to support my household (single mom here), I wanted to work from home, and I wanted to own my time. 

When I began, online businesses and remote work didn’t exist. Everything was analog. Graphic designers worked with type galleys, rubylith, and Rapidograph® pens. They worked in design firms, ad agencies, or art departments. If one wanted to show a portfolio they had to make an appointment to see an art director or arrange a drop-off. Portfolios were actual books or cases. Freelancers worked in house, in a studio, in an office, or at home.

Then came the Apple Macintosh, and then came the internet. With each, everything shifted.

As I look back over the years — decades, actually — I have to acknowledge that there were many times I made the wrong decision. I didn’t like cold calling or selling so I didn’t do either regularly. I didn’t build my brand. I accepted every project I was offered. I invoiced at the end of projects, and was often stiffed by clients.

Did I ever think about quitting and going back to a full-time day job? 
Yes, on occasion.

But my reasons for freelancing and my purpose kept me going.

A difficult question

The questions of quitting is significant for self-employed creatives because:
  • There have never been more opportunities for freelancers to grow their businesses than now.
  • Barriers to entry have never been lower.
  • Technologies are making it easier than ever to run a business, build clientele, and promote your work.
But these opportunities come with challenges:
  • Ease of entry means there are more competitors
  • Technology and social platforms result in more more choices for clients, and lower prices.

I estimate that for every 5 people who start freelancing and enjoy success there is one who tries for awhile, quits, and goes back to a day job.

Sometimes quitting is okay. In fact, sometimes it’s the wise and right option.

Freelancing isn’t easy. It takes courage and tenacity to push through. It starts out being fun, like a great adventure, especially when you land your first couple of clients and get paid for the projects. 

But obstacles and opposition will show up. Count on it. When they do, it’s no longer fun. Your initial excitement fizzles away.


In his book, The Dip, Seth Godin (book link) describes this “Dip” as that time when it looks like everything’s working against you. You begin thinking it’d be better to quit than to continue.

Friends will quote that line about the insanity of doing things over and over again and expecting different results. They question if you’re being stupid for believing you can make a living as a creative.

Family members will remind you that if it’s meant to be, it should be easy.

For some, going back to a W2 job may be the right decision.

But understand that everything worthwhile comes with difficulties. Obstacles and let-downs are inevitable and should be expected.

So how do you decide?

1: Expect the dip to show up — and not just once.
The dip comes with all worthwhile pursuits.
  • The difficulties of freelancing limit the number of people who stay with it for the long haul. The dip creates scarcity. People don’t like doing hard things.
  • If it were easy, everyone would do. Consider: how many of your current competitors will still be freelancing twelve months from now?
  • Don’t expect anything to happen “overnight”. Success is the result of a series of small steps taken in the same direction. You complete a road trip mile by mile. You have to rack up those mile markers. Perseverance ( go look up the definition) is required. “Those to persevere to the end will be saved.”


2: Know your WHY.
My WHY is what kept me going through crappy times and bad clients. I believe I’m called into entrepreneurship and I’m here to do the creative work helping clients, and to teach others how to do the same. Having a strong WHY gets you through the roadblocks.
3: Accept that the challenges will change you.
I address this in my goals webinar. Achieving goals should change you. Every goal comes with challenges and even direct opposition. There’s a cost. Be willing to pay the price if you want to succeed. You can’t stay where you are. You have to change.
4: Test drives don’t get you anywhere.
If you jump into freelancing to try it out, you will not make it work. You have to be all in. So you have to be willing to press through the dips.

5: Pursue excellence in BOTH your creative work and your business skills.
If you focus only on business your creative problem-solving ability will suffer. If you focus only on the creative work, your business will suffer. You have to blend both.
So, if you find that you’re not:
  • Passionate about what you do and convinced about entrepreneurship
  • Willing to pay the price
  • Working to be the very best at what you do
  • Don’t have a solid WHY that comes from the core of your being (or from God),  

…then quit quickly and stop spinning your wheels.

That’s my best advice for those asking if they should quit freelancing.


© Alvalyn Lundgren. All international rights reserved.

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