Your Success Matrix

Jenni Gritters
5 min readDec 29, 2023

Freelance editor Ami came to me with a request: She wanted to write an e-book about freelancing. It was a goal that seemed to make a lot of sense from a practical perspective. She’d been freelancing for a decade and had a lot of wisdom to share. She also had a lot of followers on social media, and had recently started teaching workshops about how to pitch editors, too. She wanted to know: Could I help her figure out how to launch the e-book without burning out?

I signed her up for a month of coaching and we started to dig into this goal. First, we looked at her vision for her business: She wanted a lean operation that provided her with quality client relationships, a calm mood, and lots of time to do things other than work (like garden, go on long walks, and play pickleball).

We talked about what she cared about in her business and life: Making enough money to pay her bills and save, being seen as a trusted expert by her clients, and feeling generally able to manage her depression symptoms.

Next, we audited her clients: Some were working well for her, and some of the relationships were feeling a little stale because of low pay and internal drama.

Then I asked: What does your version of success look like, this year?

Her answer: “I think I should probably try to hit six figures of income this year. I should publish that e-book so I can have some passive revenue. And I should probably hire an assistant to help me. I should probably diversify my services too, right?”

That tell-tale word: SHOULD. As one of my wonderful IPEC teachers told me last year: “Should” is “could” with shame attached.

The freelance and small business industries are full of practical “shoulds” — ways to market, structure our businesses and days, and scale up. But in my work as a coach, I’ve found that a “should” is the absolute LAST thing you should follow. When that word pops up, you’re usually talking about an obligation, not a heart’s desire. If you pursue that obligation, it runs counter to your internal needs; over time, this misalignment causes burnout.

Ami’s answer to my question about success was telling because it included very few of the things she cared about. She loved having a lean business. She loved working in a calm manner. She…



Jenni Gritters

I’m a writer and business coach for freelance creatives based in Central Oregon. I write about the psychology of small business ownership.