Asking Not Asking #32: Questioning Next Steps
TINA ESSMAKER / Creative Coach
Dear Tina,
I've been meaning to write for a while now. I love your column and seeing your career transition has been really inspiring. I'm writing because, like many, I'm unsure about where I'm at in my career and what my next steps should be.
I have been lucky to have exciting and fulfilling full-time jobs prior to starting on my own as a freelancer a bit over 4 years ago. It feels like everything is moving along nicely. I keep getting jobs and finally have a decent base of repeating clients and my name is getting some recognition and value. However, somehow, I find myself at a bit of a loss in terms of career growth and my path. I no longer feel super excited about jobs unless it's something completely new or a client that aligns with my vision and values. I think freelance life has shifted my focus from doing what I love to worrying too much about money and business. That makes me feel like something is not working. I want to be excited about what I do again, I've always been a very passionate individual.
I keep asking myself if I should change my approach and what my next step should be: should I form an official studio and try to grow that (scary, but possibly interesting if I want to continue as an independent artist)? Or continue on my own (no overhead or mgmt complications, also no need to think/find someone to partner with)? I find that at the moment doing everything myself allows me to remain worry-free and keep a lot of freedom, which I really like, but I wonder if it’s hindering long-term growth.
Thanks for taking the time to respond,
Questioning Next Steps
Dear Questioning Next Steps,
Thanks for following the column. I’m glad you finally decided to reach out and write to me!
First, I want to help you normalize where you’re at in your career and the questions you’re asking. If we could see our entire paths, that would take away some of our anxiety, but it would also take away the excitement of discovery along the way.
It sounds like there are two things that are top of mind for you about your future: 1) What is the best approach to growing your business with confidence? 2) How do you find excitement again? Let’s start with the first inquiry.
You said, “I think freelance life has shifted my focus from doing what I love to worrying too much about money and business. That makes me feel like something is not working.” You are not alone in feeling the tension between enjoying the process of creating work and confronting the financial pressures of running a business. Every freelancer has to confront this at some point. Most freelancers will confront this challenge at multiple points during their path.
Spending too much time worrying about the business robs you of the joy of creating. You became a freelancer because you wanted more autonomy and control over your career. Being independent gives you an opportunity to increase creative freedom and choice. It can be easy to lose sight of everything we have to be grateful for, including being in control of our own destiny, when we are worried about money.
“Spending too much time worrying about the business robs you of the joy of creating. You became a freelancer because you wanted more autonomy and control over your career.”
How can you compartmentalize business and creativity so you have time set aside for each that does not overlap? If you are in the middle of working on a project and are thinking about balancing your books, it’s going to be a distraction and will steal your energy for the work. It can be helpful to have regular check-ins on the calendar to do business items and regular blocks of time devoted to creative work. That way, if something business-related pops into your head while you’re working on a project, you can jot down a note and know that you have time set aside to address it soon. Without that kind of intentionality, you can be tempted to address questions and concerns as they come into your mind.
Treat the time you set aside to create as sacred. No email. No notifications. No thinking about business. No money matters. Perhaps there is a ritual you can come up with that signals when you are about to enter into a block of time for creating. Maybe there’s a mantra you can tell yourself, like, “I am setting aside the next two hours to create without interruption. Everything else can wait until I’m done.” It’s straightforward, but helps you set your intention. Business matters will always be waiting for you, but you get paid to do the work, so you need to be able to focus and invest your energy into your creativity.
You ask if you should remain solo and keep handling everything on your own or perhaps start a studio. Which will help you grow? Is it hindering you to remain solo? You may want to check out the book, Company of One, by Paul Jarvis. Although I haven’t read it yet—it’s on my list—I do subscribe to Paul’s newsletter and have found his insights to be helpful. The book is about how to become a sustainable and profitable company of one. Paul’s belief is that growth can happen in many different ways and that doesn’t always have to mean bigger—often it means smarter. Reading the book could be great homework for you and give you questions to think through, the first being, is the traditional growth model right for what you want.
“Treat the time you set aside to create as sacred. No email. No notifications. No thinking about business. No money matters. Perhaps there is a ritual you can come up with that signals when you are about to enter into a block of time for creating.”
However, many people do enjoy starting and building a studio and find that’s the path for them. If you did that, it would be a new and exciting challenge. Perhaps it would up your levels of creative satisfaction. But it would not disconnect you from the business and money conversations you are having now. You would still think about business and money, even if you have a partner. And if you have employees, whether full-time or contract, you will feel even more pressure financially because you will want to ensure financial stability for them.
When you think about your long-term growth, what would success look like? That might be a wonderful writing exercise to help you clarify and uncover your goals. Financially, what would success look like—what is the actual number you want to hit? Creatively, what would success look like? Opportunity-wise? Platform-wise? The only way you will be happy with your growth is if you own the vision for it. Don’t feel pressured to follow other people’s paths into growth. What works for them may or may not work for you.
Also, as you think about growth, it’s important to consider ways you can maximize your impact. You can only put in so many working hours each day, which means you need to charge a rate that sustains you. Also, are there ways to earn income that don’t require hours of labor? For example, consulting 1:1 requires active labor, but writing a book that people can buy only requires that you write the book once. Passive income can be a great way to augment the work that requires labor. Even as an artist, illustrator, or photographer—or someone who creates any form of visual work—you have more to offer beyond that. Can you create a class or write a guide or identify some other way to contribute your expertise in a way that people crave and would pay for? These are all ideas to consider as growth can often be hindered by our literal inability to take on anything more because of finite hours in the day.
I recently listened to astrologer Chani Nicholas on an episode of the podcast Hurry Slowly in which Chani talks about this conundrum as a business owner. While she no longer does 1:1 readings because it wasn’t scalable for her, she has a monthly astrology forecast that people can pay for and download plus she just wrote a book. So she remains a company of one but is giving people more opportunities to interact with her work. In the episode, she noted, “It’s really about what you bring to your work because a million other people are going to do some version of what you’re doing. And the only real power or ‘je ne sais quoi’ that we have in terms of our professional self is the way in which we bring ourselves to our work.”
To echo Chani, what are the ways in which you bring yourself to your work? How can your approach feel more aligned with who you are? What makes you unique? What are parts of your story and journey you can integrate into your work? How does your personality come into play? How can you show up to the work in a way that feels good for you? These are all deeply reflective questions that will require time to answer. But if you can get into alignment with how you want to grow you will feel less pressure to take the path that others have and you will begin to feel pangs of excitement again—although know it’s natural to not feel excited all of the time. As you answer the questions I’ve posed, you will begin to identify what the path could look like, and it might not look like either of the ones you proposed in your letter.
Remain open to surprise,
Coach Tina
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Asking Not Asking is a bi-monthly column written by Tina Essmaker, a New York City-based coach, speaker, and writer who helps others live into their possibility. To be considered for the column, send and email to tina@workingnotworking.com with a short note about where you're at and where you want to be, and make sure to include the following:
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