How 5 Days Can Change You

Five days ago I flew away from paradise.

I was fortunate to attend a 5 day Mastermind conference in Cabo San Lucas called CaboPress. The event is the creation of Chris Lema, one of the foremost authorities, and kindest mentors, in the WordPress community. Chris speaks and writes about business leadership, entrepreneurship and public speaking (to name a few!).

Group at CaboPress

The CaboPress Group 2016

To say Chris is awesome might be an understatement! Many people say it, and it is true – Chris is a generous, wise and caring person. I met him in 2013 at WordCamp Baltimore and during our brief conversation he made a huge impact on my path as an evolving WordPress freelancer.

I read about CaboPress in 2015 and was tempted to go. I eventually chickened out, worried that my business was too small to fit in with others attending from large, established companies. I told myself if my business continued to grow, I would apply to go the following year.

Fast forward to 2016 and now I am looking back on an amazing experience!

I wrote a thorough review on the plane coming home, but I have to say that the past 4 days, where I have been revisiting conversations and ideas from my time in Cabo, and putting into action lessons I learned, have really highlighted the value of this experience.  So first I want to share the lessons I learned at CaboPress, followed by a description/review of the event itself.

What I Learned At CaboPress

I had never attended anything like this before. Leading up to the event, I was excited but also nervous. I know that I have a good deal of “Imposter Syndrome” and the idea of being surrounded by successful, well-known developers and business owners was scary. I gave myself lots of pep talks about not putting myself down, not talking about how I have been a “Mom First” for most of my career and not being self-conscious. I set goals of absolutely making the most of the time I would have with others, both to glean advice, but also to meet interesting people, hear their stories and share whatever I could with them as well.

On the way home from Cabo and for the first day or two afterward, I was sad that it went by so fast. I found myself questioning whether I made the most of this retreat. I gave myself a hard time for letting my guard down and being self-conscious, and I wished it was a few days longer. I realized that I didn’t get to talk to everyone there – it took me a while to get comfortable and get to know a few people, and with 50 people in attendance, I found there wasn’t time to connect with each person.

Over the past two days, however, my regrets and self-consciousness about what I didn’t accomplish, have evolved into immense motivation, excitement and gratitude for the CaboPress experience. The key lessons I took away from CaboPress are:

  1. I should take more pride in my business and take it more seriously.
    Something I heard on a number of occasions was “Don’t try to be someone else” and “Don’t compare your business to someone else’s.” Everyone starts somewhere, and everyone makes mistakes, especially when they are starting out. Evolving from a full time “Mom” for the past many years into a full time “business owner” almost by accident, my path has not been as deliberate or thorough as others, but I have still made something impressive on my own (with a lot of help from the WordPress community and my local network!). My definition of success should be based on constantly improving my skills and service to the best of my ability, instead of being based on how I measure up to my peers.
  2. My time is worth something.
    An awkward moment for me was when I asked a question about spending more time than I expected on a project and how that “didn’t really cost me anything,” meaning, I lost no money out of pocket. I wanted to stick my head under the water after I brought this up, because I think people around me were shocked! They encouraged me to view my time as an expense, and they were right – it helped me to hear it. As a matter of fact, upon my return from Cabo I sat on a panel discussion on Freelancing at WordCamp Baltimore, and heard my same words coming out of someone else’s mouth … and I was able to share a lesson from Cabo within 48 hours of returning, which felt awesome.
  3. Processes, communication and detailed estimates are critical to success.
    Jennifer Bourn, one of the hosts, had some very helpful tips on automating client communication, setting expectations, vetting potential clients and clearly defining scope. I am excited to put into action some of the methods her agency has used to make their business more profitable. I read lots of blog posts and listen to podcasts about processes and business practices all the time, but somehow hearing a description and ideas in person really sunk in for me.
  4. I do not want to become a “Big” Agency – and that’s OK.
    It was inspiring to meet and talk to executives at large agencies, as well as others who are smaller or solo. Perhaps if I were 15 years younger, the opportunity to create a company with several employees would be appealing. But at almost 50, and having worked almost completely by myself for the past 20 years, I realize that this is not something I want. I did confirm, however, want to grow and collaborate with my business partner Evelyn at Nice Work, and a conversation with Chris Lema helped me define how to move that business forward as well. I loved talking to other businesses about their remote teams, hiring and ways to structure a business to grow without adding salaried employees and taking on too much risk.
  5. I made lasting relationships, friendships and connections.
    I met so many caring, interesting people. Some were in the WordPress space, and others were related to it, as a number of attendees brought their families. I loved seeing partners in business and in life/marriage together, and spouses supporting their partner and caring for their children. While this was a working retreat, there was a lot of down time and relaxation, and I enjoyed meeting children and partners as well as other WordPress/business owners. I have already heard from several people who are keeping in touch and I look forward to seeing familiar faces at WordCamp US next week.

    Tara Claeys with group at lunch

    Lunch Group #7

  6. Carrie Dils is awesome!
    Carrie was my roommate. I am a fan of her podcast, had met her in person once, and we exchanged messages and tweets many times so I felt like I knew her a bit before we got there. I admire what she has accomplished and am excited for her new projects, such as her SEO Bootcamp with Rebecca Gil and her Real World Freelancing book with Diane Kinney. But even putting her successful business aside, I discovered that Carrie is a kind, and super fun person to spend time with. She introduced me to lots of great people at CaboPress and gave me some helpful advice, too. I am very grateful!

    Carrie Dils, Tara Claeys and Erika Moore

    Me with Carrie Dils and Erika Moore

  7. I want to go back!
    Whether it is next year or several years down the line, I hope to go back to CaboPress, having implemented many of the things I learned this year. And, next time I will take a chance on getting sea sick and go on the Pirate Cruise, too!
View from window at Grand Fiesta Americana Los Cabos

View from my room!

Many other CaboPress attendees have written excellent summaries of the experience. Following is my more detailed review, for those who want to know what it was like, but you can also see what others have to say as well.

The CaboPress Experience in Detail


The Grand Fiesta Americana Los Cabos

The Grand Fiesta Americana Los Cabos Resort

CaboPress is the best “conference” you will ever attend if you are able to go. To call it a conference does not accurately describe the event. It is also a kind of “Mastermind Retreat” where business owners, mostly in the WordPress space, get together to casually exchange ideas, encourage each other and network.

Sunrise in Cabo San Lucas

The sunrise was beautiful

Sunset in Cabo San Lucas

I missed the Pirate Ship adventure but saw a beautiful sunset on the beach

The format of the conference was very well thought out by Chris Lema. The resort was absolutely decadent! The property was gorgeous, with multiple royal blue swimming pools overlooking the ocean. Unlimited food and drink made it easy to relax. The quality of the food and drink was excellent, and the rooms were very comfortable, all with stunning views of the ocean. The staff was friendly and provided excellent service.

Infinity pool at Grand Fiesta Americana Los Cabos

The infinity pool is where we held most of out “meetings”

Each morning we met for a plentiful buffet breakfast. From there, we headed to the pool, where we stood in the water for two conversational sessions. Chris had several hosts who each led a conversation on different topics, from Getting Clients to Mental Health to Branding , to name a few. Chris thought of everything .. he even handed out waterproof pouches so we could take notes in the pool on our phones!

My favorite talks were about Getting Clients, Mental Health and Branding. Jennifer Bourn, who runs Bourn Creative with her husband, Brian, shared a lot of tips that were directly applicable to my business. Many people asked questions and shared ideas and experiences. Another host was Sherry Walling of the ZenFounder podcast. While not directly in the WordPress space, Sherry provided guidance on mental health and issues and feelings faced by business leaders, founders and entrepreneurs. She had a wonderful, calming presence and was an asset to the event. Steve Zengut of Zeek Interactive, Jeff King of GoDaddy and Karim Marucchi of Crowd Favorite also led talks which pertained more to larger business owners, but also topics like Estimating and Getting Clients, which apply to any business. Other hosts were Jason Cohen of WPEngine and Brian Clark of CopyBlogger/Rainmaker Digital.

After the morning sessions in the pool overlooking the ocean (How brilliant! One morning we looked out to see a whale jumping out of the water!), we met for lunch in prearranged groups. My group, consisted of 5 people from varying business types and sizes. These lunch groups added some cohesion to a large group by giving each of us a consistent “touch base” every day.

After lunch we had free time until 5 pm. Most people met up at a pool, on the beach or around a bar to continue conversations and get to know each other better.

Each evening we met for dinner, twice at the resort, and then one night at Ruth’s Chris in the city, where we were treated to an amazingly delicious meal! The last night was a Pirate Cruise. This looked like a great time, but I am prone to sea sickness so stayed behind for some exercise, relaxation and quiet reflection. I definitely had some Fear of Missing Out, but I did not want to be remembered for getting sick over the side of the boat!

In the city of Cabo

A night out on the town!

On the final morning, we said our farewells over breakfast and connections on Twitter and Facebook have been happening ever since. I am grateful for the time, lessons and all the wonderful people I met at CaboPress! Thank you Chris Lema!


Other CaboPress reviews I have seen as of this publishing:
Chris Wallace

David Payette

Scott Magdalein

Blair Williams

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