7 Big Lessons from 10 Years of Entrepreneurship

Today’s episode of Lifestyle Business Weekly is a little different. This time, I’m sharing 10 of the biggest lessons I’ve learned about building independent businesses. This episode is full of good stuff, and I hope you’ll find the time to watch.

This is in preparation for a talk I’m giving this weekend at the Pioneer Nation conference near Mt. Hood, Oregon. Note: if you’re attending the conference, skip the video for now, I think it’ll be better for you in person if you haven’t watched already.

If you like the show, I’d love to send you weekly updates including links to new episodes and links to the best articles about entrepreneurship and lifestyle business I find each week. Subscribe here »

Also, you can leave a question for me to answer on the show. Just comment on YouTube or Facebook or wherever you find the episode and I’ll do my best to answer soon.

Thanks for watching!


Kill Your Comfort Zone

Your comfort zone is holding you back.

It’s the warm bed in the morning that you don’t want to get out of.

It’s the Candy Crush you use to avoid something more important.

It’s the safe job keeping you from taking the plunge.

It’s staying home instead of doing something new.

It’s what is known versus what could be.

Comfort is stagnate.

Growth is uncomfortable.

By definition, growth is the opposite of comfort, of stasis, of stagnation.

Growth happens outside of your comfort zone.

Growth happens when you take on new challenges.

Growth happens when you embrace the unfamiliar.

Growth doesn’t just happen. It’s a conscious decision to do something you don’t feel comfortable with, something that challenges you. It’s a decision to do something even though you don’t know what the outcome will be.

Growth leads to a potential for rewards that comfort will never bring.

Growth is a calculated risk.

You can’t live within your comfort zone 100% of the time and expect to grow. The more time you spend outside of your comfort zone, the more you’ll grow.

Want growth? Kill your comfort zone.

Lifestyle Business Weekly Episode 4: Nomad List and the Facebook Productivity Tax

In today’s episode: the best places to live and work around the world, building and working on remote teams and two viewer questions about social media.

Ask a question for an upcoming episode. Just leave a comment on Facebook or YouTube, or reply to my weekly email and I’ll do my best to answer on the show.

Connect with me here:

Weekly email: http://corbettbarr.com
Twitter: https://twitter.com/corbettbarr
Facebook: https://www.facebook.com/corbettbarr
Instagram: https://instagram.com/corbettbarr
YouTube: http://youtube.com/corbettbarr

Scott and Corbett

Scott Dinsmore, I Will Miss You Forever

The world lost one of the most exuberant, supportive, caring, generous and motivated people on Saturday. I lost a dear friend who will leave a hole in my heart forever.

Scott Dinsmore died in a terrible accident while climbing Mt. Kilimanjaro in Tanzania with his wife Chelsea. They were eight months into a year-long around the world trip. Scott and Chelsea were literally in the middle of the trip of a lifetime.

It’s hard to express the grief and sadness I’ve felt since getting the news. I don’t think it has really sunk in. I keep feeling like he’s going to walk through my front door or call me or send me an email. Then I remember he’s gone and I feel empty and alone.

Scott was an inspiration to thousands through Live Your Legend and his TEDx talk on How to Find an Do Work You Love, which now has nearly 3 million views.

Scott was the most sincerely passionate person I know in most areas of life, but especially when it came to believing each of us deserves and has a responsibility to find and do work we truly love. Scott would tell anyone who would listen about his vision for making the world a better place by motivating people to ditch dead-end jobs in favor of finding what we were meant to do.

I met Scott on October 20, 2010. It sounds ridiculous, but we met at a “tweet up” I hosted in San Francisco, where a few of us interested in blogging and entrepreneurship met up to share ideas and get to know each other.

Scott’s wife Chelsea made fun of him for attending the tweetup. That was something I’ll always remember about Scott — he didn’t care if people made fun of him, for listening to Taylor Swift, for wearing pink pants, for doing endless push-up and burpees challenges during the day, for hanging out with the “blog squad” as Chelsea used to call me, Leo, Barron and other bloggers Scott spent time with.

I remember the day we met as much as any day I spent with Scott. That’s the kind of impression he made in every interaction. He was larger than life. Scott lit up every room he walked into and made every person he talked to feel like the center of the universe. He was more than charasmatic, and it was 100% genuine. I’ll miss his energy and zeal so, so much.

That first conversation we had lasted hours, and quickly turned into a working relationship. Scott had been blogging at a site called Reading For Your Success. I knew his energy and that site were mismatched, and I suggested he should re-brand the site to serve a bigger purpose. Scott hired me to help with the re-branding, design and launch of his site, which became Live Your Legend in July 2011.

When I search my Gmail for conversations with Scott I get 1,930 results. I don’t believe I have shared that many emails with anyone else, ever. I can’t believe I’ll never receive another.

Within the first handful of conversations about Scott’s new site, the word “revolution” came up. I didn’t realize then what Live Your Legend would become, with hundreds of thousands of readers around the world. Scott truly started a revolution. Here is one of the earliest visions Scott shared with me about Live Your Legend:

…most importantly to just take the world by the horns and do what you are best at and what you're meant to do. I want to inspire people to give a shit about their lives instead of listening and following all the time.”

Scott gave me a lot of credit for Live Your Legend, but that was just part of Scott’s character. He was always complimentary, always willing to share the spotlight, always enthusiastic, and ever supportive of his friends. What started as a mentor-type relationship quickly turned into camaraderie. What I learned about life from Scott was far more valuable than anything I taught him about business.

What impresses me so much about Scott’s work and life is how he led by example. More than anyone I know, Scott embraced each day as a precious gift. He took the world by the horns, and did what he was best at, what he was meant to do.

Live Your Legend Think Traffic WDS Meetup

The last time I saw Scott was March 22nd, 2015. He and Chelsea came to visit Jessalyn and I at our winter home in Mexico. They were just a few months into the year-long around the world trip, and we were so happy to get to host them for a short stop in our town. Scott was his usual over-the-top self.

One night at a dance club around after a long afternoon tequila tasting session, Scott and I challenged a couple of local Mexican gentlemen to a dance off. These guys were good. One of them did a pretty mean robot. I pulled out all my stops and did the worm. Scott sealed our win with a full minute of walking on his hands and dancing with his feet in the air. None of us saw that coming.

I loved the parties we had together. Scott and Chelsea’s holiday party was legendary in San Francisco. Our going away party last year was especially memorable. We were moving to Portland, Scott and Chelsea were setting off on their trip, and our other close friends Leo and Eva had just moved to Davis, CA. It was the end of an era in San Francisco, one of the most special and transformative periods in our lives.

wine country

The fun and parties with Scott were amazing, but what I’ll cherish most were our regular long conversations about business and life and everything in between. We debated and discussed travel, marriage, having kids, simplicity, money, philosophy, mentors and what life meant to us. We had so many of these conversations, and I’m lucky to have recorded several of them.

As I’m writing this, I’ve temporarily forgotten he’s gone. Remembering the times we had together has brought him back. But now I remember there will be no more, and it brings me to tears. Scott was a once-in-a-lifetime friend. I’m lucky to have many great friends, but there was only room for one Scott Dinsmore on this planet, and now he’s gone.

I don’t want to stop writing, because ending this post makes it all feel real and final.

Here are some other memories of Scott I’ll never forget:

  • When we arrived in Croatia with two other friends, as part of Jessalyn and my 10-year wedding anniversary, there was a bottle of champagne waiting in our room… from Scott and Chelsea. They had spent part of their honeymoon in Croatia and especially loved the town of Hvar. We stayed in the hotel he recommended and he sent us a bottle of champagne.
  • Scott had a “Mission jacket” he wore whenever he visited my neighborhood, the Mission of San Francisco. Scott lived in the Marina, which was the opposite side of town in multiple ways. The Mission was gritty, and Scott had a healthy respect for the people in our hood. His “Mission jacket” was what he considered hip enough to fit in, and it cracked me up every time.
  • Scott was kind enough to join the Fizzle crew to celebrate the launch of our new blog, and I blindsided him with a question about being arrested. He handled the question with aplomb, along with our incessant harrassment about his favorite pink pants.
  • Chase Reeves, Scott and I spent a few days at a cabin in Tahoe to redesign Live Your Legend last year. The three of us confided in each other about the depression and anxiety that plagued us as entrepreneurs. It was a heavy weekend, one that took our relationship to a new dimension.

For those of us who knew Scott and will miss him forever, we’re so lucky to have his spirit captured on video and audio, and in the millions of words he penned for the community at Live Your Legend.

This sadness I feel is so heavy because Scott was so god damned special. He gave so much, and he had so much left to give. I’m lucky to have known Scott and to have spent as much time with him as I did. I can’t imagine how impossible his loss must feel to Chelsea and Scott’s parents and his life-long friends. I’m so sorry for you all, and I hope our memories of Scott can bring us all some joy one day.

I love you Scott. You showed me how to live with a sense of urgency, and a passion for helping others live better lives. You made me a better person, and I will always be grateful. You left a big dent in this world, my friend.

Please, if you’re reading this, keep Scott’s spirit and work alive. Find something you love to do, and live the life you were meant to. Surround yourself with people who care. Believe in yourself. Live life to the fullest.

Here is Scott’s most popular work, his TEDx talk on finding and doing work you love:

For more memories of Scott, read these posts by Leo and Chase.

Lifestyle Business Weekly Episode 3: A Roadmap, Comparing Yourself and Building a Business Around Your Ideal Lifestyle

It’s Episode 3!

In this episode:

  • A Roadmap for Small Business Success
  • Comparing Yourself to the Wrong People
  • Building a Business Around Your Ideal Lifestyle

Thank you all for the amazing feedback and comments on the first two episodes! I appreciate the support and enthusiasm :)

Keep those comments rolling in. Leave me a note over at my YouTube channel or Facebook page, or if you’re a subscriber of Lifestyle Business Weekly email, just hit reply on any message and say hi.

You’re Just One Person. Stop Comparing Your Work to Big Teams and Deep Pockets

I just launched the Lifestyle Business Weekly show, and I’m happy with how the first two episodes turned out. I’m hungry to make it better, but still happy with episode 1 and 2 as a starting point.

But damn, it’s soooo easy to look at all the amazing videos out there and feel silly for even trying. Last Week Tonight is one of my favorites lately. It’s so well produced, and such fantastic research goes into every episode.

John Oliver and his team spend 15+ minutes covering a single topic and keep my attention every step of the way. These aren’t fun/fluffy topics either. His best segments are on meaty topics like net neutrality, the wealth gap and nutritional supplements.

But something really struck me as I watched the last episode of the Daily Show with Jon Stewart as host. Watch the episode if you haven’t already. There are amazing insights into what a great boss Jon Stewart was, and how The Daily Show had so much stamina and stayed so relevant for over 16 years.

Later in the episode, John pays tribute to all the people behind the scenes of each episode. A camera tours the offices in a long single shot and they call out all the people and departments and contributions that go into each show. There must have been over a hundred people on the team.

On shows like this, you sometimes see just one person plus a guest on camera for 20-30 minutes an episode. The shows are amazing, but they should be. There are 100+ people on each staff, and they all work 60+ hour weeks putting the show together.

You, on the other hand, are ONE PERSON. You spend maybe a few hours on each blog post, or podcast or video. Yet, you compare your work to work produced by teams and deep pockets.

Does this seem like a fair comparison?

I’d say you’re doing pretty damn well, actually, when you consider how few resources you actually have.

Your goal isn’t to produce Last Week Tonight. Your goal is to produce the best content one person can, the best content you can produce right now, given your other responsibilities.

You’ll get better over time. If you want a fair comparison, look at what up-and-coming YouTubers are able to do with a team of one or two. That will give you something to shoot for over the next year.

And then, stop comparing yourself to others for a while. Put your head down and do the work. Look up in a few months to see how you’re doing, then get back to work again.

Stop comparing yourself to others. Put your head down and do the work.


NEW! Introducing Lifestyle Business Weekly The Show

Publishing the Lifestyle Business Weekly email has been so much fun over the past two months. You’ve given me fantastic feedback, and the subscriber base is growing by leaps and bounds every week.

Now we’re taking the next step. Lifestyle Business Weekly is now a weekly video show, and you can watch the first two episodes today!

Episode 1: Finding Yourself & The Truth About Passive Income

Episode 2: Humble Beginnings, Business Plans and 100 Days Without Fear

If you want to support the new show, here’s how you can help:

1) Please watch an episode when you have time (episodes will be 10-15 minutes long) and send me your feedback. Just leave a comment on an episode and tell me what you’d like to see me do with the show.

2) Please subscribe to my YouTube channel, and share the show with someone you think would love it.

New episodes will be published weekly. If you’d like an email with a link to each week’s show, signup for the Lifestyle Business Weekly newsletter.

Thanks for watching!


I’m LOVING this new show for entrepreneurs from the @fizzle guys. Lifestyle Business Weekly:


Toxic Culture in a Company of One

In the past couple of weeks since the big story about Amazon’s broken work culture, the web has been abuzz with stories of big companies with long hours, demeaning politics and impossible standards.

As you may have read in the articles like Work Hard, Live Well, “the research is clear: beyond ~40–50 hours per week, the marginal returns from additional work decrease rapidly and quickly become negative.Long hours backfire for people and for companies.

In other words, working more than 50 hours a week can lead to negative productivity.

Many big companies have a BIG problem when it comes to culture. That’s the main reason I left the corporate world over a decade ago.

However, the same culture problems can and do affect tiny companies as well, all the way down to companies with just one person.

Maybe this describes you. Are you building a business all by yourself? How honest are you being about the culture you’re building for yourself?

Don’t fall for the idea that you can “out hustle” everyone else month after month. Even hustlers need a break, and when you don’t take time off, your business pays the price when you eventually burn out.

Work hard, but be smart. Be honest with yourself about how much time off you’re taking, and how much you need to perform at your peak.

Respect the research and your limits. There’s an optimal amount of time to work, and that amount is much less than the “hustle” crowd preaches.

Don’t Find Yourself. Create Yourself.

Life isn’t about finding yourself. Life is about creating yourself.
– George Bernard Shaw

This is so true.

It’s ridiculous to think each of us has just one perfect passion in life, or that there is only one thing that we’re on this planet to do.

Finding yourself or finding your passion is a misnomer. You can find a passion or a version of yourself, but ultimately you have to create the person you want to be. You have to pursue something deeply before you know if it’s right for you.

If we’re lucky, each of us will have many things we’re passionate about in our lifetimes.

Finding yourself is the result of working hard, and creating the person and the life you want. Don’t worry about getting it right, just worry about doing interesting, important, epic, valuable work. The work will lead you.

Don't Find Yourself. Create Yourself.

Don’t Find Yourself. Create Yourself.

Little Wins Matter

When you’re in the middle of a big audacious project, it’s easy to get down on yourself. The feeling of finishing is renewing. Delaying any chance of finishing for too long feels like defeat. This is why it matters so much to break your projects down into bite-sized pieces.

If your project is feeling too long, take a minute to set yourself up for a little win. Could you ship a sneak preview? Could you take a quick detour to get something done from your list that matters? Little wins matter, if only because they make you remember how good it feels to ship something.

Corbett Barr

A weekly curated email of useful links for people interested in lifestyle businesses and independent entrepreneurship.

Page 1 of 6

Happy ! Thanks for reading.

RSS   |    Archives   |    Newsletter