Over the years, I’ve noticed an interesting pattern of migration for professionals moving between nonprofit work, corporate careers, freelance roles, and entrepreneurship in search of something better. Economic conditions can also require us to shift for survival. When stability matters most, people often return to traditional jobs that offer a consistent paycheck. When flexibility and independence feel more important, they brave the unknown.
And, shifting between new workspaces doesn’t always provide the freedom we’re looking for. Sometimes, real autonomy requires changing more than our circumstances, it requires a deeper change in the systems around us. After encountering the same challenges at multiple jobs, we may come to realize that changing the workplace often results in encountering the same systemic issues, just in a new environment. The system itself was never disrupted.
Looking for Freedom
During the pandemic, I left my nonprofit career to pursue running a business. I was about ten years into my career, and I’d noticed a pattern across the organizations where I worked. Teams were often over capacity, with too few people and too little funding to deliver everything leadership promised.
Employees kept the work moving because real people were impacted by our programs. In some cases, I saw my coworkers putting in 60 to 80 hours a week to meet their goals, often for less pay than they could earn somewhere else. The mission made the sacrifice feel necessary, but over time, there was always a risk of losing control of our own time and energy.
Some people moved into corporate roles for better pay and more stability. But those environments brought different pressures, including performance measures that didn’t always reflect the full value of someone's work and the risk of losing a job when keeping that employee no longer suited the business.
I moved toward entrepreneurship because I wanted more freedom. I could decide when to work, choose which opportunities to pursue, and say no. But I also found myself working around 60 hours a week. Without a team or clear structure, I had to figure out what mattered, what to prioritize, and what work would actually pay off. Every decision came with consequences because I was responsible for everything.
I’d gained flexibility, but I hadn’t escaped the pressure.
Different Workplaces, Same Systemic Challenges
Every work environment comes with its own circus. A nonprofit can lack the funding or staff to support its programs. A large company can struggle with departments that don’t share information or coordinate their work. A small business can lack the processes, roles, and resources needed to operate well.
These problems look different, but they can create similar experiences for the people doing the work. Employees and founders feel overwhelmed, undervalued, excluded, or responsible for fixing problems they didn’t create.
That doesn’t mean every workplace is broken or that changing jobs can’t help. Sometimes a new environment really is a better fit. But when the underlying problems come from how work is organized, changing employers may only trade one set of pressures for another.
Designing Better Ways to Work
A systems thinker looks beyond the immediate problem to understand how people, processes, resources, decisions, and outcomes connect. Instead of asking how individuals can work harder to meet expectations, we ask whether those expectations make sense in the first place.
Are responsibilities clear?
Do people have the resources they need?
Are teams working toward shared goals?
Do leaders understand the impact of their decisions?
Are we measuring meaningful outcomes, or simply rewarding activity?
These questions help organizations identify where their systems create unnecessary pressure and what needs to change. We can’t eliminate every workplace challenge, and no single role can solve every problem. But we can stop treating recurring struggles as individual failures when the system itself contributes to them.
Sometimes, finding a better place to work is the answer. And sometimes, the bigger opportunity is to change how work works.
