One of the developments that freelancing’s recent rise has brought, is the abandonment of the career ladder. It may not be a whole-sale abandonment. Freelancers can still go through phases or stages of their career, but the traditional “ladder” doesn’t apply to freelancers. In many ways, this is a good thing. The promotional structures companies used to implement were often based on nothing, or on unimportant traits and skills.  There were some positives to this system though. It gave workers a sense of where they stood in their career, where they needed to go, what they needed to learn, who they needed to suck up to, and so on. After freelancing for a while, one can feel untethered, with no markers to let you know where you’re going, or how far you’ve come.


One of the best ways to measure your career progress is your income. Are you making more now than when you started freelancing? Most likely you have records of your average monthly and yearly intake year over year. Take a look. Has this number gone up? If you had an income goal 5 years ago did you reach it? Look at your frequency of work, the average length of time between work, and the most common way in which you find work. Are you getting jobs more consistently? Is the time between your jobs shorter than it was 5 years ago? Do you find yourself getting offered more work than you did 5 years ago? These are all pretty basic rubrics one can use to determine their career progress. Many of you might already know the answers to these questions. We all have memories of how our career was 5 years ago as opposed to now, but it can be helpful, and give you more confidence, to actually see this change. Keep records. They can be pay stubs and contracts, but they can also be journal entries. Every few months or so, take a little time and write down how YOU think your career is going. After all, the best way to measure progress is to create your own checkpoints. Have you been meeting those?


It’s important to know that humans are very poor predictors of how their future selves will feel about any given decision. We seem to fool ourselves into knowing what we’re going to be like in 5 years from now. We’re nearly always wrong.  So, it can be helpful to get an outside perspective. A good way to figure out what we want our futures to look like is to talk to people who are already there. Who in your life has a career that you’d like to emulate? Ask them how they measure their success, and how satisfied they are with their current situation. Using the careers of others can help us understand our own standing, and create more accurate goals for us to aspire to. When comparing your career to the career of others, it's important to have more than one role model or exemplar. If we base our career on only one person, it can cause our path to be too narrow and make us feel as though we have to fit a mold we never will. Having multiple career exemplars gives you a broader brush to paint with, and more ways to gauge your progress.


It’s important to not compare yourself to others too much. An excess of comparison only leads to disappointment. Your life is your own and you define its successes and failures. That’s more true for a freelancer than anyone. Success in freelancing is in many ways, still a new concept. That’s kind of awesome. That means there is no particular place, person, or thing you need to be, for people to think you’ve succeeded. You get to decide that. The hard part is the deciding. One way to figure that out is to look at the careers of people completely outside your industry. It can be surprising how many people, no matter the trade, have very similar career goals. Some people may want a certain title or a corner office, but often people look for signs of progress closer to home. Do I have enough savings to take a vacation? Am I spending more time with my kids? Am I traveling as much as I’d like? These are career markers we all share no matter the gig. Ask your accountant how they measure career success? Ask your doctor, your client, your uncle, your friend who just moved to Argentina.  There is probably some overlap in what they all see as career success. Much of what we want out of our career is its ability to support our lives. When thinking of where you want to be in your career, make sure to factor in where you want to be in your life.

Avoid that moment of existential dread in the back of an Uber on your way to the airport by taking some time every once in a while to assess where you are, where you’ve been, and where you’re going.