Tips For The Unrelenting Creative: How To Decide Between Career Stability Vs. Career Flexibility

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Hi everyone,


I’m coming to you about thirty minutes late this week. So sorry for the (slight) delay in getting the latest edition of my newsletter out to all of you. Our slow crawl back to “normal” is taking a toll on my ability to complete tasks on time, which makes this recent tweet all the more timely:



Thanks so much for reading this week’s newsletter and I hope you’re having better luck spinning all those plates.



How To Decide Between Career Stability Vs. Career Flexibility


Think of your decision between career stability and career flexibility as a dial you can turn from left to right. Starting at zero you can turn the dial all the way up to ten, depending on which side of the dial defines you best. The higher the number on the dial, the more financial risk you are comfortable taking in your life and career. There are no right or wrong answers, and everyone is different. Your job is to figure out the type of career path you would like to pursue.


My creative, dreamer, big idea mindset wants to throw caution to the wind and pursue flexible work that I love so I can be free to create. My realist tendencies push me to find balance. Without health insurance and a regular salary, my career would be far more unstable. Out of necessity and desire, I have always turned my dial towards career stability.


Most creatives I advise dream of career flexibility. They would gladly trade some financial stability in order to have time to engage in meaningful career pursuits. Before Covid, our workforce as a whole seemed to be moving in this direction. In his report, Freelancing and the Economy in 2019Adam Ozimek, chief economist at Upwork found that 75% of individuals in Arts & Design fields identified as freelancers, the highest percentage out of any field. In fact, creatives were leading the charge when it came to career flexibility. Ozimek said, “The improving labor market means that, for the first time since Freelancing in America (FIA) began in 2014, there are as many freelancers who view freelancing as long-term as there are that view it as temporary, at 50% each.”


The rise of Covid brought flexible work to a halt. While none of us expected the quickness and intensity of the change to our way of life, the virus exposed the real underlying challenges many Americans simply chose to sweep under the rug. In their 2018 report titled Financial Fragility in the US: Evidence and Implications, the National Endowment for Financial Education noted that “More than 36 percent of working adults in the United States are financially fragile and cannot come up with $2,000 in 30 days. This vulnerability is more prevalent among women and those with low income or low education, but this study shows that a broad cross-section of the American population is at risk, including middle-aged and middle-income families.” Americans are abysmally bad at planning for minor setbacks, let alone the enormous challenges we all have faced during the pandemic.


The virus has left creatives in a precarious position. A creative’s livelihood is mostly dependent upon shared experiences in close proximity. With social distancing now the new normal, creatives have had pivot to find a new path towards a sustainable career.


Creatives have been reaching their audience for generations by combining the business skills they developed (mostly on their own) with the expertise they gained in the academy. While most of our society discredited this type of work because as they were pursuing careers rooted in stability, creatives quietly built their careers as freelancers.


Regardless of your chosen path, it’s important to figure out whether to turn your dial towards flexibility or stability.


My first memory of making the decision between career stability and career flexibility came when I was 25. I was just wrapping up a Master’s degree in Bassoon Performance at the University of Michigan and, at that point, I knew I wanted to continue on for a Doctorate, but not before taking some time off from school to let my master’s degree sink in.


This was a pivotal moment in my life and career. When graduation day hit, I knew that many of my friends would stay in Ann Arbor with roommates in order to teach private students and gig in the area, solidifying their version of a flexible career and essentially extending their college experience.


The post-degree pressure from friends to stay in town pulled me towards the type of flexible, freelance career most artists in their 20s were pursuing. That life was tempting to me and, by keeping my costs low in Ann Arbor, I knew I would have been able to carve out a life for myself and enjoyed my time as an artist. Yet, on graduation day, there were other factors that gave me pause.


First and foremost, I had accumulated over $26,000 in student loan debt during my master’s degree. This debt discouraged me from pursuing a flexible career, especially because I also had a car payment and a growing amount of credit card debt. Second, I was set to get married in August of that year, just a few months after graduation and wanted to be closer to my fiancée, who was working on a Doctorate in Physical Therapy at Old Dominion University in Norfolk, Virginia. I could have stayed in Ann Arbor and my wife and I would have worked it out, but being together in Virginia was way more important to me than pursuing a flexible career in Michigan.


With those two factors in mind, I moved back to Virginia and became an elementary school music teacher. My starting salary was $31,000 a year. I had a degree in music education so the expertise I gained from the degree I earned in college provided both financial stability and a foundation of work that set me on a path for success as I considered the next steps in my career. For two years, I taught, continued to practice, and took any gig that came my way. Looking back, I likely would have made about the same amount of money pursuing a flexible career in Michigan as I did teaching in Virginia but it was a moment that I realized just how important a stable job was to me. The stability was comforting and my work gave me the flexibility to pursue my art in a way that was meaningful and empowering.


Bringing context to the stability vs. flexibility question


You can’t make a decision about stability vs. flexibility without bringing agency (“The thoughts and actions taken by people that express their individual power.“) and structure (“The complex and interconnected set of social forces, relationships, institutions, and elements of social structure that work together to shape the thought, behavior, experiences, choices, and overall life choices of people“) into the discussion. (Source: ThoughtCo) These two concepts have a direct connection to the life we would like to have for ourselves.


Most creatives I work with focus on agency, choosing to work towards a perfect life, one where they are completely in control of their ideal career path without considering the other factors that play into the career they would like to pursue. When creatives focus on agency first, the discussions I have typically focused on creating beautiful things and not necessarily how they might make this work in the world outside their studio. Agency gives individuals the power to think for themselves and act in ways that shape their experiences and life trajectories.


Agency can take individual and collective forms. One of the biggest places individuals feel stuck is when they have a low level of agency in their lives due to the social structure surrounding them. In other words, someone (or something, hello Covid) is making your life and career decisions for you. Having the agency to stay in Ann Arbor would have allowed me to express my ability to pursue the thing I wanted most in life, my art. Structurally, I couldn’t do it. My income would have been unpredictable and low, while my expenses would have been high right out of the gate. Those two factors severely limited my ability to have agency and a flexible career. On the flip-side, my full-time job in Virginia actually allowed me to have a solid financial footing while simultaneously letting me pursue income beyond my day job as an educator, dramatically improving my agency.


I think one of the reasons the Covid has been such a punch in the gut is because we have had our agency taken away from us due to the structural challenges of the pandemic. For an extended period of time, we have not controlled our future, the virus has. That made it very difficult to be creative. Now that we are starting to come out of the shelter in place orders and the vaccines are flowing, our agency is still stifled because it is going to take quite a bit more time for us to recover from the economic fallout that occurred with so many people out of work for so long.


The pandemic has enabled me to take stock of the things in my life that I can control, which allowed me to express my individual power. After the initial shock of how dire this pandemic actually was, I started to find moments of reclaiming my agency (IE, writing this newsletter). Over time, I grew to appreciate the different opportunities available to me as a creative.


You will get back to a sense of normalcy. When you do, it’s important to factor agency into your decisions. Much like the freedom to create, having agency in your life is one of the most important factors when developing a career as a creative. Just like determining a path between career flexibility and career stability, the amount of agency you desire will determine your path.


Given the idea that you have the agency to be in control of your career, there are three pathways to consider. Each pathway has a low and high level of agency, depending on your desired path and the external structures you face.



I hope this post gave you some things to consider as you determine which direction your career flexibility vs. career stability dial should be turned and I’d love to know how this post resonated with you. If you have time, shoot me an email with your thoughts.



  • How to create great content: One of the biggest challenges I have when it comes to building an online presence is developing a routine for creating and distributing great creative content. Check out this incredible article on effective content creation, complete with in-depth examples and an excellent flowchart.
  • Read this if you’re having trouble getting started: I love this (very short) post by Ben Pettis titled The Cult Of Done Manifesto. Whenever I have trouble launching a new idea or project, I refer to this note for a little jolt of reality and action.
  • Work on the weekend now so you can do it during the week later: I work on my big ideas in the late hours of the night or on the weekends because I often need a creative outlet to keep me motivated during the week. Author Chris Dixon argues that the smartest people in the room work on their big ideas during the weekends so all of us can enjoy their creations during the week in a decade. While I don’t consider myself the smartest person in the room, I do love to muse about the idea that the things I create in my spare time now will pay off ten years down the road! 
  • How creatives can pursue a sustainable career: One way to achieve a career rooted in flexibility is to pursue work that decouples time from money. The problem is that this type of work is often very high risk. In this outstanding Twitter thread, Daniel Vasallo makes the case that creatives should pursue flexible work by making several small bets instead of one large bet in order to find traction in their career.
  • Jacob Collier + Yebba: Check this (very short) video of Bridge Over Troubled Water out. If you’re like me and you want to hear more Yebba, here is an additional four-minute video, enjoy! ​

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Nate Zeisler is the Dean for Community Initiatives at the Colburn School in Los Angeles. He envisions a world where students majoring in the arts have a clear path to a sustainable career, where creative minds are empowered and inspired to rule the workforce, and where access to the arts is not just for the privileged few, but for all.

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