1099 progress markers

by Dale Davidson March 18, 2026

A humorous stick figure cartoon depicting the contrast between an independent consultant taking a nap and a W2 employee working hard to get a promotion. The first half of the cartoon shows a stick figure independent consultant lounging in a hammock between two trees, with a laptop closed beside them, indicating a relaxed work environment. They are depicted with a peaceful expression, taking a nap. The second half shows a stick figure W2 employee at an office, surrounded by mountains of paperwork, frantically typing on a computer. Above the W2 employee's head, there's a thought bubble with a trophy labeled 'Promotion', symbolizing their hard work and ambition. The scene is exaggerated and whimsical, emphasizing the differences in lifestyle and work approach between the consultant and the W2 employee.

When you're in a W2 career, it's easy to know if you're making progress.

If you are, you'll make more money, get more promotions, and work for companies with better brands.

If you are a 1099, a lot of that goes away, and it can be unsettling.

So how do you know if you're doing well as a 1099?

I haven't been a solo 1099 for a while, but here's how I know I was making progress at the time:

Making more money without working harder
Finding it easier to get new projects
Increasing amount of free time to pursue side projects and hobbies
Decreasing amount of stress in my life
Increasing number of Friday afternoon naps

You can borrow my measures of progress, or you can come up with your own.

I have a friend that works for herself as a 1099 full time for one company.

She feels successful because she has above average vacation time, lots of flexibility, and high earnings relative to her area's cost-of-living.

She has no desire to find new projects or expand the business.

We're wired to want what others want, so when you remove yourself from one of the main group contexts that establish those wants, you have to dig deep to find out what your true desires are, and then measure your progress against those desires.

Or, you can just promote yourself from "consultant" to "Supreme Allied Commander/CEO" on your LinkedIn page ;).

Want the full playbook? Check out Going 1099.