Learning from other solo entrepreneurs

This business mastermind retreat was one of the most powerful “conferences” I have ever attended.

I use quotes around the word because although Statement is a conference, with a website and everything, it’s a conference in a format I’ve never experienced before.

There were no speakers.

No sessions.

No expo hall.

Instead, Stefanie and Emma used a combination of careful attendee selection, luck, magic, an amazing vacation home in upstate New York, and an idea to put everyone in the “hot seat” for 30-45 minutes so each person could get insight from the group to turn this three-day slumber party into a nonstop business strategy session.

It was insanely powerful.

It’s funny, because most people there were in what I’d consider my cohort. Not everyone started at exactly the same time, and a few of the attendees were new enough to this particular corner of the internet that I was meeting them for the first time, but a similar narrative could be told.

Generally speaking, attendees started blogging in the early 2010s, then morphed either their URLs or their focus (in many cases, both), and are now working for themselves.

As Brent would say, we’re all addicted to workahol, and we have big dreams.

The same struggles kept appearing in each hot seat.

How do we find the time to do everything?

How do we outsource when training someone to help us sounds like “just another thing” we should be doing?

How do we approach brands to get sponsorship opportunities or ambassadorships?

How do we deal with impostor syndrome?

That last one really stuck with me, because impostor syndrome is something I thought would just “go away” after I got to a certain point.

But no.

Because once you start to “level up,” the stakes are higher, and you worry that you’re one misquote away from the career you’re building. Or that sure, one company wants to work with you and pay you a corporate amount of money, but what if they were a fluke and you’re going to be found out to be a fraud?

It’s dealing with low-level anxiety all the time.

It made me think that this is how Hollywood actresses must feel. Sure, that $5 million dollars they made on their last movie feels great, but what if that’s the last time they ever get to act?

I feel impostor syndrome quite acutely, since I’m starting over, for what feels like the 95th time since I bought FrugalPortland.com in 2011.

But talking to the group, and realizing that the business I’m building and the services I’m offering fill a very real need, give me motivation to keep pushing forward.

Or, I should say, more motivation.

I’ve burned my ships.

Landed in a new land.

And now, it’s time to start building.

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