A peek behind the scenes of my business

I’m taking a break from my usual musings on being human to give you a little behind the scenes look into how I run my business.

Last weekend my assistant extraordinaire/business manager/we’re still coming up with the appropriate title, Kathleen, joined Mike and I in our hometown of Portland, ME for a weekend of business visioning, clarifying, goal setting, deliverable defining, and some good old down and dirty logistical planning.

A critical aspect of my business and life philosophy is that if it’s not fun, it’s not worth doing. So often we associate increasing our income, expanding our business, and even being of service with hard work and sacrificing having a good time for productivity.

I want to share a few key choices we made for the energy and agenda of the weekend so you get an example of what it looks like to mix business AND pleasure. These are the most important aspects that I think made our weekend meeting successful:

My mom and Kathleen enjoying a latte from a local coffee shop.

Ingredients for a Fun, Productive, and Meaningful Meeting


1. Eat well, and locally if possible. As soon as we picked Kathleen up from the airport we went straight to Pai Miyake, one of Portland’s best restaurants featuring delectable Japanese food, most of which is grown or raised locally 20 minutes away at the Miyake farm. A well fed body makes us more grounded and more highly functioning. And investing your money in local, organic agriculture is good for the planet. Win-win.


2. Get lots of sleep. We knew we had a limited amount of time together to go over TONS of ideas, projects, logistics, plans, and visions. And we also knew that if you’re tired, it doesn’t matter how many hours you have to work – the work just isn’t as good. I didn’t set my alarm either morning of our retreat and my ability to stay present and actively engaged the whole weekend was a direct result of being well-rested. I’ve been to plenty an event where the leaders wear you down emotionally by making you stay up well past midnight and those who leave to take care of themselves are not only frowned upon, but are often chastised. The “no pain, no gain” and pushing your physical limits to the point of exhaustion model has no place in my company. How you do it is what you get. The more ease, joy, pleasure, fun, and well-restedness that goes into a project, the better the results will be.



Getting ready to board the amphibious Downeast Duck Tour on a break.

2. Take breaks often. We had luxurious meals all weekend and took breaks for coffee, for a birthday party, and for the Downeast Duck Tour. We laughed, we chilled out, we played with adorable babies, we learned a ton about Portland, and we nourished our bodies, minds, and spirits. As a result when we were working we were super engaged and great ideas flowed. When you take good breaks you can get more done in half the time it would take you if you powered through all the time.


The results of our branding mind-meld.

3. Mind-meld starting with the assumption that every idea is a good one. In an effort to come up with a tagline that accurately answers the question “what do I do” we got a HUGE white board and started throwing out every descriptor we could think of when it comes to my brand. We gave one another the freedom to just shout things out. In the beginning stages of mind-melding or brainstorming, assume that every idea is a good one. You might say something really silly. But the act of articulating something silly may lead you to the best idea you’ve ever had that you may not have ever had if you hadn’t said the silly thing first. When you’re in mind-meld mode let yourself say ridiculous things. Let your editor go on a coffee break. Says something cockamamie. Lubricate the brainstorming process with unconditional acceptance and you’ll be amazed with the gems that are revealed.

We took a break on Casco Bay and toured the Portland Harbor.


4. Get outside. A very wise friend of mine once reminded me that if you can’t see the sky there’s no way that you can see possibilities for yourself. So when laying plans for expansion and business development, be sure you get outside to see the sky. When we’re out in nature we remember that everything is connected and that life itself is a miracle. When the energy starts to stall at your meeting, open the door and take a walk around the block. Take your shoes off and put your bare feet on the grass. Go searching for seals in the harbor. You’ll be reminded of the majesty of the universe, you’ll think bigger and better, and you’ll have better ideas.


5. Bounce.  You can take this one literally like Kathleen did (on the ball to the left) or you can take it metaphorically. Good ideas do not come from stagnation. They come from movement. Get out your yoga ball and bounce. Stand up and do a few hip circles. At the very least, wiggle your toes. And remember to remain in the open, playful state of bouncing. You’ll be more agile in your thoughts and therefore open to new ideas that wouldn’t have been possible if you stayed still.


6. Don’t take yourself too seriously. I know I’ve said it here before, but it bears repeating:

Anything work taking seriously is worth making fun of. 

That goes for your business just as much as for anything else in life. Find ways to make your meeting more fun. Bring gifts for everyone. Have a playlist and dance breaks. Have everyone start by introducing themselves and telling their favorite joke. Play soccer with a yoga ball. Watch silly YouTube videos. Your business will grow more if you have fun while building it and if you don’t take yourself too darn seriously. Trust me. This really works.


Kathleen posing by the beginnings of our brand brainstorm.

8. Dive deeply into the “why” before you begin to iron out the “what” or the “how.” This one is probably the most important of all. On the first morning of the weekend when Kathleen asked me about the bigger vision of my business and brand I immediately tapped into the “why” of what I’m doing and started getting teary. I told her that what I truly want is to have kids and be a really present mom. (Anyone who’s heard me talk about this live knows that it usually brings me to tears. That’s how I know it’s real.) I also told her that I want to not only be an example for a new model of present parenting that comes from financial freedom instead of stress, but that I want to give people actual steps to get there. I told her that I see myself as part of a movement of people having the freedom to choose to come home to what really matters to them. As I muddled through my last tear-filled thoughts I turned to Mike and asked him if he was on the same page. He nodded and told us that he wouldn’t be here if he didn’t want those same things. We spent the weekend filling in the gaps in terms of what we’re going to create and how we’re going to deliver it. But if we hadn’t started with that deep dive into the truth of what we’re really up to, the WHY, the entire weekend would have been wasted. Don’t bother asking yourself “how” or “what” until you know “why.”


Next time you’re planning a meeting, consciously find places to bring the nurturing, to bring the heart, to bring some giggles, to bring in movement, to get out in nature, to have a hell of a good time, and to remember why. Your sense of purpose and your bottom line will thank you.


  • Best Bosses in the World. So grateful for such a beautiful, generous, productive, hilarious weekend. xoxo

  • Morning Kate

    I love it when people I admire and follow are cool enough to peel back the layers of their life and let me, us, others have a glimpse. Having had an opportunity to spend some time with you, I could imagine how this all unfolded! Lucky Kathleen. Way to create and build from the right open space in your heart and mind. I look forward to see where this all leads :)

    xo Johanna

  • Hi Kate,
    I really enjoyed reading this post today. I love your approach (your assistant/manager must love it too!). I also believe that you need to focus on what drives you, what gives you meaning and purpose- the “why” and not the “how”. It’s really easy to get confused without understanding the “why”, isn’t it?

    I can’t wait to see what unfolds from this amazing weekend~

  • Jacqui

    Hey Kate and fellow New Englander! Thank you kindly for showing us inside your business jam sessions. I completely admire the “why” in what you do. I am a stay at home mom (by choice) and am trying to get my biz up and running (absolute crazy pants). I consider myself to be a completely present mom which is great but leaves such little time for making the biz part happen. Sometimes i wish that i had this all figured out before kids (i am 32) but have really come into my own since having my girls. I have just taken RHHBchool and am on my way (i hope) to be financially free…Keep going girl and if you ever want to chat over tea about all things being a mom- i am your girl! XO jacqui

  • This is so flipin brilliant. So many favorite frames to this article… When you write I feel like I’m in Main with you! Love the movement advice. I strongly believe in a playlist. Great path way to the creative!

  • Love it Kate! Mixing business with pleasure makes life much more fun!

  • I’m closing one door of my life and wondering what door to open next. Everything is up for grabs at the moment, and I haven’t got a clue where to start. Or I didn’t have a clue until I read this post, Kate. I start with the big why and not the how.

    PS: I loved getting a behind the stage pass to your business and what a business visioning exercise looks like in your world. It seems FUN is the operative word. I’m good with that! :)

    See you tonight at the Firestarter Camp Fire.

  • Wow way to lead with your heart Kate so courageous! And I love a great office chair :)

  • Kate you so lead with your heart, way to go sister goddess! Love that MIke is on the same page and you are so transparent YES! MOre love on the planet on a result:)

  • I see myself as part of a similar movement too! I want to help moms be prepared -before they’re moms. I am just at the very beginning of doing that:) Sort of in the trenches with an 18 month old and a newly turned 6 year old:) So many people told me “you can’t prepare for motherhood.” And that was so not true. If you need any help from Philadelphia -I am here! I love your posts!

  • Shelley

    This post was terrific and so timely!

    It was on the eve of one of the first meetings of a sort of women’s mind-share group I helped create that we call “The Next Best Thing”. We are a group of women who have had the blessing/opportunity to be present, full time moms and now these kiddos are all in school full time and we’re looking for our next dream to fulfill while we continue working on the motherhood dream!

    We weren’t entirely sure where this group/idea would take us and your post was so helpful! “Diving deeply into the why” really gave focus to our brainstorming. Thank you so much for the inspiration and peek into your session. So incredibly helpful!

    If ever you’re in the Madison, WI area, let us know! We’d all love to share our passion for motherhood with you and learn more from you, specifically about financial freedom. Until then, please know your blog posts are inspiring and full of real world ideas. Thank you! Thank you! Thank you!

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