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Photo credit: Chris Guillebeau via cc

Nearly ten days have passed since I attended the inaugural Pioneer Nation event in Portland. I’ve had time to reflect on my experience and now it’s time to share.

It’s nearly impossible for me to describe what actually went down over the course of three days. Imagine a conference packed with aspiring and seasoned independent entrepreneurs, small business owners, and freelancers – all passionate about making a bigger difference and dedicated to their cause.

As a relative newcomer to the independent entrepreneur scene, I knew one thing for sure. This is my tribe! Almost every conversation, every speaker, every workshop, every shared moment – fueled my desire to make a difference by doing more meaningful work in a bigger way.

If I had to come up with an overall theme for the event, it would be this:

Just say Yes!

Say yes to sharing your work.

Say yes to being bold.

Say yes to serving others.

Say yes to giving yourself permission to be wildly successful!

Say yes to thriving.

Say yes to getting paid what you’re worth.

Say yes to challenges.

Say yes to collaboration.

Say yes to failure.

Say YES!

If you’re contemplating whether to really go for it as a thriving independent entrepreneur, I think Eminem sums it up best in the opening lyrics from ‘Lose Yourself’:

“Look, if you had one shot, or one opportunity To seize everything you ever wanted. One moment. Would you capture it or just let it slip?”

I’ve contemplated the best way to review my experience of Pioneer Nation and I’ve come to the conclusion that it will be nearly impossible to capture the event completely and with brevity.

Therefore, I’ve decided to reflect on the most important takeaways from each speaker and workshop leader. Here we go.


Chris Brogan“Own Your Path”

As the lead-off speaker for the conference, Chris Brogan encouraged everyone to own their path wholeheartedly, declare who you are, tell your story, make someone a hero, and thrive by offering ultra personal service.

And one of my favorite moments came when Chris told everyone that he just had a conversation with the Universe and it had something to say: “You are depriving the Universe by not giving everything you have right now.” (i.e. you have permission to stop playing small and instead to get your ass in gear and do the work that you know you are meant to be doing)

Jen Adrion & Omar Noory “Say Yes to sharing your work.”

I loved these two! Jen & Omar shared how they turned a simple idea into a half million dollars in revenue last year. So much for starving artists!

They also shared what all the naysayers were telling them along the way (notice the picture in the collage above that shows real comments made about their art – it’s a good thing they didn’t listen!)

Most importantly, Jen and Omar encouraged us to say yes to what makes you happy – then make what makes you happy – then share it with the world.

Nathan Barry“People don’t teach because they’re experts. They’re experts because they teach.”

This is simply brilliant. We become the expert in our field when we decide to share what we know with others. This message really hit home for me because I tend to think I need to learn it all or know it all before I can share it with others. Not true! Stop being a course/certification junkie and just get out there and teach what you know.

Laura Roeder“View hiring as a profit center. Take the leap and free up your time to create.”

Laura is a master at her craft and when she speaks, I listen very closely. Laura challenged the audience to take a close look at how much time we are wasting by doing work that someone else could be doing better and more effectively. Snap! This one hit me right in the gut.

The bottom line is that in order to play a bigger game you’ll need to hire a team that can support you. Take the first step and map out what someone else could be doing and then give it to them – even if you just start with an hour a week.

Stop wasting your creative energy doing the things that someone else could be doing – probably much better than you. For me, this would be accounting, bookkeeping, editing and posting my podcast, and social media management. You get the picture. Now go find someone to delegate to.

Shenee Howard “Do the things you know how to do first. Then create the things you want.”

Oh Shenee! You made me laugh and smile so much. Shenee’s advice was such a great reminder to start with what you know and build from there. I’ve been guilty of comparing myself (and my work) to others and then getting off track. And then I usually have to scale back to doing what I know.

By focusing on what I know, I can build upon that knowledge to move towards the things I want most. The path of the independent entrepreneur can be filled with doubt and anxiety so it’s important to build your business on a solid foundation while enjoying yourself along the way.

Rena Tom“Just because you can doesn’t mean you should”

Rena is a rare breed – part thriving creative, part brilliant businesswoman, and part donut connoisseur. Rena encouraged us to be selective about our creative endeavors and not bite off more than you can chew (unless it’s a donut). 😉

Chase Reeves“Make people’s lives better in small and meaningful ways.”

Between the funny stories and clever impersonations, Chase delivered a remarkable message to stay focused on making people’s lives better. If we can connect with people and then deliver real value to them, we increase our odds of succeeding exponentially on this wild ride of independent entrepreneurship.

Oh yeah. How could I forget his ode to Fernet. This may go down as the most creative argument in favor of  drinking this quirky Italian liqueur…EVER! Chase freely credited this unique drink for allowing him to meet his current business partner, cure his stomach ailments, and expand his growing business. Well done I say!

Lori Allen“Hurry up and fail…on any new path.”

Lori shared her amazing journey to career success on her terms. And the common thread to her success has been taking risks and failing more than anyone else.

In a culture where it seems people are rewarded for looking good, fitting in, and following the rules, it’s important to understand one of the things that enables independent entrepreneurs to succeed. And apparently it’s the ability to fail faster and more than anyone you know. Who knew? And that’s not the end of it. As failure happens (as it surely will) it’s important to be okay with it and consider it a sign that you’re on the right track.

Andy Hayes“Building an audience is like sprinting a marathon, only to realize at mile 26 that you’re just getting started.”

I attended Andy’s two-hour “Build Your Audience” workshop and it was like crawling inside my customer’s skull and seeing through their eyes for the first time. Andy shared his recent experience of how his own audience has exploded in the past few months and it was brilliant.

If I had to boil it all down then I suppose my top takeaway is that it’s vitally important to understand how your customer sees the world and why you fit into that picture. The other thing that really struck me was that it takes hustle to build an audience. Just because you build something doesn’t guarantee that people will pay attention to it. You must tell them about it.

Kari ChapinYou have to get to the point that you’re enjoying what you do so much that you’re doing it no matter what.”

This was a knockout shot. So simple, yet so impactful. Once you begin enjoying your work and delivering value for the sake of doing it, watch out! I’ve found this to be a turning point in my business and it was such a great reminder that you need to make a decision to show up every day, every week, every month, and do your thing – no matter what!

Willo O’Brien“Your number one job is to keep yourself as happy and healthy as possible.”

Thank you Willo for the important reminder. If you think working harder will make you happy, maybe it’s time to consider new options. Options like making self-care a priority and finding ways to bring more magic into your life.

Listening to Willo was the equivalent of my Soul receiving a much-needed massage. And the funny thing is that once my Soul began to feel rejuvenated, it was much easier to answer her empowering questions: “What brings me joy?”  “What support can I bring on now to 2X my business?”  “How can I duplicate myself?”  “What brings me income?”

Brian Clark“Deciding what not to do is as important as deciding what to do.”

As I was listening to Brian talk, it hit me. This is the guy behind Copyblogger! One of the most successful content marketing companies…period! And then Brian told the story about going through law school and becoming a lawyer until he couldn’t stand it any longer.

He talked about what it means to be an independent entrepreneur and about when he finally realized that he was basically unemployable. And once you realize that you’re unemployable, it can be one of the most liberating feelings in the world because now you get to decide what you will and what you won’t do. So be careful about what you say “no” to and be even more discerning about what you say “yes” to.

Chris Guillebeau

I don’t have a direct quote from Chris but I will say this. He is the embodiment of someone that knows how to create community, add value and have fun.

Thank you Chris for understanding the needs and desires of independent entrepreneurs and for creating this fantastic environment for us to connect, learn, and grow.

And here’s to all you brave pioneers that willingly choose this bold and brilliant path.

In gratitude,


P.S. Which quote is your favorite and why?

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