Observations and Inferences

I started working from home in September of 2017, just around 3 weeks after my Dad died. I was 22 years old.

Needless to say, it was not an easy time to live in my brain.

It was also a challenging time to be thrust into self-management. Between the grief and the shame spirals that inevitably accompany such a profound loss, I had a hard enough time remembering to eat, let alone exercise complete autonomy over my working life and schedule.

As we gear up toward the one-year mark of self-isolation, I’ve found myself thinking a lot about those first few weeks I spent working from home in 2017.

I was living in Orlando at the time, in a condo nestled between the downtown area, several highways and an extraordinarily loud train we’d named Clarence. I slept on the couch most nights, because for some reason depression and my bed simply did not mix (and also it was a really great couch).

In the mornings, I’d pry open my laptop in the dark—curtains drawn, blue light...

Earlier this week I sent out a poll on Instagram. 129 of you answered. Of those who answered, 73% of you said you want to be self-employed. You mentioned things like wanting freedom, independence and control over your schedule.

What's more: A whopping 98% of you agreed with the idea that "I have to learn to manage myself if I want to be my own boss."

When I asked what the challenges were with doing that, the answers rolled in for nearly 24 hours straight. The most frequent responses? Motivation, discipline and "knowing where to start."

So let me do what I do best: Give you a place to start.

It starts with an offer. It starts with knowing what you want to give to the world. How you want to help people.

The trick is not just offering something — most of us spend our whole life offering things to people, be it love, admiration, labor, etc. The trick is to offer something that is scaleable.

Being scaleable means it's a product or service (or "productized service") that can be easily...

One of the most common questions I get from new clients is this: "Should I create an online course or a membership?”

When you start researching eLearning, it’s incredibly easy to get caught up in everyone’s ~proven methods~ for success. After all, eLearning is a massive industry that’s estimated to climb to $325 billion in the next five years. With that kind of revenue, it goes without saying that there are a good number of successful people in the mix.

The problem is, eLearning is by no means a get-rich-quick industry. Those success stories marketed across the Internet? The ones screaming at you from Facebook ads and following you around every YouTube video? Those creators are successful as a result of spending YEARS growing, launching, failing and trying again.

The ONLY guaranteed way to achieve eLearning success is to launch. Launch, learn and—you guessed it—launch again. Plain and simple.

My clients know this because in the...

I’m not a morning person.

Note: This was written in January 2020, and since then I have grown to enjoy mornings, which I credit to my cat and Julia Cameron's The Artist's Way.

Unless forced to by an early flight or a car alarm, I rarely rise before 8 a.m. In the mornings I am groggy, impatient and completely useless.

Growing up, mornings were probably the largest source of conflict between my mom and I. It was always the same: She’d wake me up gently, I’d open one eye, she’d leave the room, I’d fall back asleep. You can imagine what happens next.

This video by Desi Banks captures it perfectly.

Let me be clear: It’s not that I don’t want to get up early. I’d love to be the kind of person that rises naturally at 5:30 a.m., exercising and meditating before the rest of the world is awake. Every now and then I do have a good week. But most of the time, I’m a snoozer.

“So what?” You may be...

Guess what I did last Monday?

Absolutely nothing.

OK, that’s a lie. I woke up at 7 a.m. and was out the door with a grocery list by 8 a.m. I took my sweet ass time in Whole Foods, inspecting bags of clementines like the feds. Once I got home, I diiiid send a few emails and answer a calendar invite. But I just couldn’t shake the feeling that I had nothing to do.

Winter is a slow season for many of us, especially people with small businesses like mine that primarily work with other solo entrepreneurs. Winter is a hibernation season, a time where, as the brilliant Kate Northrup put it at this year’s Business By Design Live, “the Earth dedicates an entire season to rest.”

Maybe you’re like me at the moment, in-between big clients and restructuring the way you do business. Maybe you own or operate a brick-and-mortar location and know the chillier weather keeps customers bundled up at home. Maybe you work in an office or agency and are feeling...