I’ve never had a “Real Job” for longer than nine months.

But I’ve been working since I was 12. For years, I felt insecure about my apparent lack of commitment to a corporation until a conversation with my therapist revealed there is one job I’ve had for over a decade and a half—working for myself.

It started as babysitting for cash while the mom was in the other room. Then I started as a photographer’s apprentice and started shooting on my own. I nannied. Tutored in writing. Kept nannying. Wrote for tiny newspapers. Wrote for tiny websites. Wrote for literary journals. Still nannying. Wrote for small brands and bigger brands and then launched this letter.

The through line of my meandering career is this: I like working for myself. I can do without Slack or company culture and certainly without branded vests. But instead of referring to it as “being freelance” which conjures images of chasing $400 invoices, I like to think of it as a portfolio career.

Maybe you’ve dreamed of diversifying or consulting, too. I’m going to answer some of my most-asked questions and give you a simple road map. You know me; of course there are going to be real numbers.