This just in: Business is hard.

Bill Gadless
Oct 31, 2017 · 5 min read

I recently had the privilege of spending a week with a group of some of the smartest, kindest, most driven entrepreneurs in the digital space.

CaboPress is a small, invite-only “conference” put on by Chris Lema with the purpose of bringing together a group of professionals in the WordPress community to share experiences, challenges, wins/losses, insights and even personal hardships.

It’s hard to classify this event as a “conference”, as there are no ballrooms, exhibits or suits.

Correction — there were in fact plenty of swimsuits. Chris invented this novel concept in which attendees meet in a 5-star resort’s pools every morning. Suffice it to say — you can’t imagine a better environment for sharing and collaborating with your peers.

I came in with a healthy level of apprehension.

Last year, my Co-Founder/CEO Brett Cohen attended and, upon returning, immediately encouraged me to join him for the next CaboPress. I’ve spoken at a number of WordCamps around the country (the regional conference for WordPress professionals) and have formed some great relationships in the community — but I had a couple of reasons for trepidation.

First, CaboPress is kind of a “who’s who?” of the WordPress world. It’s inevitable when joining any group consisting of the “best” to experience a bit of imposter syndrome. Do I belong? Will I be welcomed? Does everyone know each other? Is everyone smarter than me? Will I have anything to offer?

Second, seeing this is an event specifically for WordPress professionals, I always have to wonder if I’m technical enough to hold my own in such a group. I’m an agency sales and marketing guy — I don’t really speak the language of plugins and gits.

Openness breeds openness.

From the very first in-pool session I joined, “Hiring Lessons” by Tony Perez, any reluctance I had was gone. Tony, a former Marine who went on to grow Sucuri and recently sold it to GoDaddy, is as about a compelling speaker as you will ever meet. It’s not just his insights, but the one-of-a-kind delivery style only Tony can pull off. He’s straight no-BS and he puts his audience at ease by avoiding corporate and technical jargon. From his experiences with hiring and firing, to the lessons learned through the growth and eventual acquisition of Sucuri, I think I speak for the collective CaboPress group in saying that Tony’s presence as a host was a significant highlight.

But the beauty of CaboPress is that it doesn’t end with the scheduled sessions. Brett and I had the pleasure of hanging out quite a bit with Tony and Sucuri Co-Founder Dre Armeda. We had a lot of laughs, shared our stories, our beginnings, our struggles. I’ve always connected well with other entrepreneurs who came up the “hard” way. No silver spoons, no MBAs from Wharton — more like a lot of hustle, risk and innovation. I also would like to thank Rebecca Gill for her candor and openness. Rebecca was kind and trusting enough to openly share her roots, the path that she’s taken to become a nationally-recognized SEO expert and educator, and even her future goals and aspirations.

The relationships formed with these great folks are what makes CaboPress (and actually the WordPress community on a whole) so special. There’s no pontificating, lecturing or even educating, per se. It’s merely a bunch of people with similar pains and objectives all getting together to share.

A professional’s perspective …

Another highlight of CaboPress for me was a session titled “Mental Health”, by Sherry Walling. Sherry is a licensed psychologist who consults with entrepreneurs regarding interpersonal conflicts, burnout, anxiety, productivity, existential angst, major transitions, and personal balance. The minute you meet Sherry, you somehow instantly become totally unguarded and comfortable spilling all of your entrepreneurial pains and struggles with her — and that’s what made her session so impactful. A pool full of us all opening up and sharing our issues — not about sales, staffing or technology — but rather the emotional aspects of our business that keep us up at night.

So what did I learn?

Well, I learned a lot of things. I learned about Mastermind Groups during a great discussion by iThemes Founder Cory Miller. I learned about how Anil Gupta of Multidots is helping clients and agencies augment their development staffs. I learned about other entrepreneurs’ businesses and objectives, like those of Josh Eaton and Katie Elenberger.

But the most compelling thing I learned from my week in Cabo?

Business is hard.

And by “hard”, I don’t mean insurmountable. I don’t mean this in a whining, “poor us” way. I don’t mean for one second that it’s not worth the worry and doubt, sleepless nights, the reoccurring chest pain …

Rather, I think it’s important for all of us entrepreneurs to know that it’s hard for everyone.

It’s hard when sales are good and bad.

It’s hard when you’re fully-staffed and shorthanded.

It’s hard when clients are happy and pissed off.

It’s hard whether you’re a CEO, a designer, developer or a sales and marketing pro.

It’s hard whether you have a strategy or you’re flailing aimlessly.

It’s hard whether you sell products or services.

But you know what? That’s okay.

It’s inevitable for a business person to feel that “things are supposed to be much smoother than this.” That everyone else must be doing things better. That you’re behind the curve. That you should be further ahead than you are. That everyone else is doing better work — and in a more efficient fashion.

These are normal feelings. We all have them. And if we didn’t have them, we’d never get better. By no means am I suggesting you stop doubting yourself; in fact continue to doubt yourself every day. But take comfort in the fact that everyone else out there hustling (like you) is dealing with the same syndromes, every day.

And get out there. Attend some meetups, conferences and networking events — in and out of your industry. In addition to learning about others’ pains and challenges, you’ll also find it quite encouraging to learn of all of the things you’re doing right.

Bill Gadless

Written by

President of emagine, a national digital marketing agency for Healthcare and B2B. A leader in Enterprise WordPress development.

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