Shifting from "Should"

Well, it was a good run, but it looks like my self-employment days are over.

Just kidding. (Check the calendar if you need more context.)

But actually, I am going back to work… for you.

I've been pretty inconsistent when it comes to publishing new Self-Employment Sidekick content. Flexibility is a double-edged sword that way. You can set your own schedule and objectives. You can also choose not to stick to any of it.

I had to give more time and attention to some other projects recently. But I'm ready to recommit to showing up and supporting you and other early-stage and aspiring entrepreneurs.

Over the past couple of months, I've had several conversations with people who feel confused and alone. They want to build something of their own, but they don't know where to start, or which move to make next. They're overwhelmed by the paperwork, the technology, the messaging. And they don't have many trustworthy people in their corner to hear them out, let alone offer any guidance.

I want to help them. More than that, I need to help them. I truly believe that's a big part of what I'm meant to do, and why I've experienced everything I've experienced up to this point: to offer clarity and connection to other folks navigating their own self-employment journey.

And one way I can do that and open up doors for more connections is to write this newsletter. So here we are.

Should vs. must

Real talk: I don’t always know what to write about each week, and there’s always plenty of other projects, shiny objects, other distractions vying for my attention. It can be easy for me to lose focus and motivation to write or work on a new video. In fact, it’s been a few weeks since I last sent a newsletter. I know I should post more often. I should be more disciplined. But “should” is a terrible motivator.

What actually sustains consistency is knowing your must. Not a vague sense of obligation; a real, personal reason why you must [enter your task here].

My must isn't complicated. It’s you guys.

Somewhere out there, someone is figuring out how to go out on their own for the first time. They're scared, they're excited, and they'd benefit from hearing that someone else has been exactly where they are.

And I know my content has been beneficial to others. I regularly receive comments on videos from folks thanking me for helping them figure something out. I got an email once from someone wondering where I’ve been after I didn’t send a newsletter for a few weeks. I don’t need to hope I’m being helpful. I know I am. And I want to keep it up. I must. Because I care about you guys.

What's your must?

If you're building something — a business, a side project, a creative pursuit — and you keep running into your own inconsistency, I'd gently push back on the idea that you need a better system or more discipline. You might just need more clarity on why it matters to you.

Should sounds like: I really ought to be further along. I should be doing more.

Must sounds like: I know exactly why I'm doing this, and that reason is bigger than my mood, my schedule, or my fear that it isn't good enough.

If you're still working out what your must is — or if you're in that place where you feel confused, stuck, or just a little alone in figuring this out — hit reply. Tell me where you're at. I read every response, and I'd genuinely love to hear from you.