Skip to main content

Hope and the End of Your Rope: Encouragement and Perspective for Creative Entrepreneurs

I’m deep in the trenches with many creative entrepreneurs via 1:1 coaching and my community, More Creative Academy. There are many creatives struggling right now. Some have had a rough year and others just a rough final quarter of the year.

A couple weeks ago, in response to one of my community members going through a rough patch in their business, I wrote the following and felt I should share it with all of you today. I hope it helps those of you who need a little boost and perspective during a possibly difficult end of the calendar year.

This image was created using DALL•E 3 and ChatGPT. I realize there is a contingent of creatives very opposed to using A.I. in their workflow. I have adopted the mindset that A.I. tools are NOT GOING AWAY and every creative should be experimenting with ways to use them in their work. Don’t hate on me for using them. Instead, put your energy into figuring out how to use them yourself.

Timing and Financial Health

You’ve checked your financial numbers and it looks like you have three months of financial lifeblood left. Three months is “forever” in business! So much can happen in that timespan, and it’s good that you’re feeling the pressure now, rather than waking up with no money left.

Faith and Trust

I’ve had many scary moments in my business. The financial swings were extreme, especially at the beginning when I wasn’t used to it. It was pure misery. However, I knew that my life plan at the time was to freelance, and then I saw the path leading me to build an agency. I had faith that I was on the right path and that “the plan” for me did not include failure. I had a family to support, and I trusted that “the plan” for my business was not for my kids to starve and for me to end up on the streets. I trusted that, and I saw rescue moments come many times.

The Eleventh Hour

Great entrepreneurs like Jeff Bezos, Steve Jobs, Bill Gates, and many others, along with my wife’s grandpa and uncles, have all experienced the scary moment when everything seems to hang in the balance on the brink of destruction. You’re joining the club of entrepreneurs and getting your taste of it.

This experience will make you a better person, able to counsel others in the future, empathize with and care for others when it’s their turn to “join the club.”

Ask any entrepreneur in the club about their experiences, and they will have plenty of “and then, in the eleventh hour, XYZ happened, and somehow we made it through!” Trust that it’s coming and take the actions now that will make it happen for you in the next three months. Know that you are paying the admittance fee to an exclusive club that has been there before you.

Forced to Pivot

Reflecting on my agency’s 15-year journey, I clearly see times when the “scary moments” forced me to reassess my entire strategy, leading to pivoting my business toward the next phase of growth.

  • When I started freelancing, I had to pivot my mindset from “job” to “freelance.”
  • In 2004-5, when I began hiring, I had to pivot.
  • When brochure websites and Flash games disappeared in 2008/9, I had to completely retool my business.
  • During the recession in 2008/9, I had to persevere on small projects while waiting for the big ones to return, which took nearly two years.
  • A trip to San Francisco for client meetings at Google turned into a pivot when all meetings were canceled. I had to dig into my contacts to find anyone to meet with, and one of those meetings led to an independent sales rep for our agency. I never would have contacted him if the meetings hadn’t been canceled.

Immediate Actions

Here are some actions I would take right now:

  • Make a list of everyone you know in any business and reach out to them. Tell them, “The business year is wrapping up. My work has been slower than normal, so I’m reaching out to see if you have any projects I could help with, such as ______.”
  • Attend networking events, Chamber luncheons, and more. Meet new people and don’t be afraid to say, “I’m actively searching for new clients, and I can help with ______.”
  • Reach out to agencies and express your interest in being on their freelance list. Highlight that during the holidays, people tend to take more time off, and you can be a great resource for them on specific project types.
  • Consider platforms like Upwork and Fiverr. I usually don’t recommend these platforms, but half the sales job is done for you, as the clients there already know they need someone for _________ type of work. They can provide some revenue in a pinch.

Don’t Believe Your Own Pessimism

You mentioned, “I seem to have fished those ponds dry.” This is dangerous thinking and untrue. Keep casting your line in the pond; the next cast might just catch the fish.

Your success is always “ONE CALL,” “ONE MEETING,” or “ONE NEW RELATIONSHIP” away. There is work out there, and clients need your services right now; they are looking for you. Go find them before someone else does.

Overcome the Fear of Being Salesy

Don’t let the fear of being too salesy keep you from reaching out to people and doing more sales. You will not be too salesy. I don’t know one creative entrepreneur who has ever been too salesy. Don’t be afraid to say, “Hey, I need some work. Is there anything I can help with?”

Part-time Work

It’s a good idea to get some part-time work to cushion the blow. Taking a little pressure off is okay. Look on job boards like Indeed for freelance opportunities. Consider freelancing for other agencies as part-time work.

These rough patches NEVER last forever and they are a great reminder to us to be grateful when things are going smoothly. Hang in there. Your adventure doesn’t end here.

Michael Janda

I am Michael Janda, an executive level creative leader with more than 25 years of experience in both in-house creative departments and agencies working with some of the greatest brands in the world including Disney, Google, Fox, ABC and NBC. I create books, courses, workshops, lectures and other training materials to help creative entrepreneurs run successful businesses.