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WishIKnewLeadTeamIncredibleTomorrow on Wish I Knew Wednesday I’m going to share how I’ve led my Jess LC and With Intention teams over the past five years and had incredible results.

(And for those who might be wondering: a merry-go-round is a nice, but not a requirement.)

If you’d like to get the email, simply sign up by clicking on the image below. This email list is also where I announce upcoming workshops and other Business With Intention updates.

If you have signed up for the Wish I Knew Wednesday newsletter, you will automatically get this email.


Hi Caitlin!
growth spurt
April 30th, 2013     |    Life

GrowthSpurtThe past few weeks months have been tough.

For a long while, my personal life was going great, but I was resistant towards my purpose in my career (helping people find their purpose).

I had the hardest time giving myself the permission to own my gift. Which is supremely amusing considering the fact that I was perpetually giving my business clients the permission to accept and celebrate their own purposes in their businesses.

For some reason I could not do the same for myself.

Then finally, after weeks of wrestling with every flawed egoic reason that my brain could think of to avoid honoring this gift, I simply surrendered. I stopped fighting my purpose, wrote my manifesto of my beliefs about purpose in the small business world, and shifted my services to better support and communicate my perspective on purpose-based business.

The results have been astounding.

When I was resistant towards owning my purpose, while knowing deep down it was there, business slowed considerably. Once I stopped hiding it and simply put it out there, clients and opportunities started appearing at a higher pace than ever before.

It feels effortless. I get to be “me” and do what comes naturally.

For a week or two, I felt a strong sense of peace about life and business.

However, a week and a half ago, a personal matter came to light which has turned parts of my personal life upside down.

Isn’t it funny how one thing can cause friction and the moment the friction is removed, another area of our life can change on a dime?

Thankfully, this matter is not health related, and I have a strong hope that this situation, though difficult, will turn out for the best.

Because this matter involves more than just myself, I cannot share the details. But I hope one day to be able to discuss this more openly in hopes that it may encourage others in similar situations.

For now, I just know that I’m experiencing one heck of a growth spurt. 

Though sometimes I feel like crying out, “when will I ever be done growing?” I realize that if I was truly “done,” I’d stay where I am.

If I was done growing before I owned my purpose in business, I’d stay stuck helping people, but never truly sharing my real gift.

If I was doing growing before this personal matter came to light, I’d feel “happy” day-to-day, without having the chance to dramatically deepen a meaningful relationship.

So though these challenges have been difficult to process while going about my daily life and working on the upcoming projects that I’m excited to share, life is better this way.

Like many intentional choices, it is not “easy,” but it is worth it.


AH-Inspired-Nashville-II-116This August I am heading to Nashville!

Though I’ve been to Nashville once a few years back (to run the Country Music Marathon with Team in Training), I’ll be back to the friendly city August 1-4.

I’m excited to speak at Amber Housely’s AMBER HOUSELY: Inspired summit on August 1-2. Amber has a great line-up of speakers for the event and I’m proud to be one of them.


Specifically, I’ll be talking about growing a business team intentionally.

If you’d like to see more details about the event and register, please check out the site and video.



After the AH Inspired event on August 3rd and 4th, I’ll be hosting the Business and Life with Intention Workshops in Nashville as well!

And as a special bonus, Amber will also be joining us to talk about the inspiring work/life/mom/business balance she juggles so beautifully in the Business with Intention workshop.

Update: I’ve also made a new registration option for the With Intention workshops. We are now offering an optional three-payment registration plan for those who prefer to break up their registration into smaller chunks leading up to the workshop.

So if you have been thinking about coming to Amber’s AH Inspired or With Intention workshop, you now have a chance to do both in the same week!


a fresh look
April 28th, 2013     |    Life

AFreshLookThis weekend Mr. Lively and I have been working on a new look for the site.

We extended the style established on the new With Intention website here on the blog.




Though we’ve decided it doesn’t feel quite as “designer-y” as the last blog look, this is first and foremost a text-driven site. And this larger format makes reading much easier.

But quite frankly, Franklin remains unimpressed. He demands to be taken on a walk around the city.

Which is exactly what we plan to do next.



Hello everyone! Jen here, and I’m looking forward to sharing another Design Your Life feature.

Today, you get to meet Allison of Halcyon Style. She is a driven and talented blogger with a passion for design and interior styling. And the best part, is she is turning her passion into her day job. Not only does she have a knack for transforming an interior space into something functional and beautiful, but she is extremely nice and an overall very positive and refreshing person.

Allison also lives in the great city of Boston. And we all know about the horrible tragedy that shook the city and our country, and if you’ve ever visited Boston, you know the people and the city are welcoming and charming. You will notice with her intentions there are beautiful photos taken of the city, so you can see just how lovely it is during this time or year.


photo by Sophie Smith

Rather than use the typical correlating image for each of my intentions, I’ve chosen instead to use images taken this Monday in the Boston Public Garden, not far from the bombing sites, after the moment of silence held in honor and memory of last week’s Marathon Bombings. It was a glorious afternoon and I couldn’t  help but capture the coming of spring through my camera lens. After a week of nothing but horrific and grim news media coming from my city I felt it important to provide some images of Boston’s beauty. As winter turns to spring, my fellow Bostonians begin to heal and move forward in the wake of tragedy.


In light of the recent horrific events in my city, this intention seems more important than ever. I cannot tell you how many times a day I’ve previously walked by the bombing sites in the five years I’ve lived here. This just shows how you never know what will happen as you go about your day. Therefore, live your life to the fullest. Try not to look too much at your past. Forget those lingering, nagging regrets. Curb the anxious worry about your future. Don’t take a moment for granted. Live your best life in the present and the rest will come in time. With this in mind I need to be better about making plans with family and socializing with friends both near and far.


One of my resolutions this year was to take more risks professionally, to take charge of building my brand and business. I finally signed up for Blogshop and not only learned how to use Photoshop to my blogging advantage, but also made helpful connections in the Boston blogging community. I also assisted Jess with her With Intention workshops earlier this year, leaving with more connections and friends as well as a sense that yes, I am on the right career path. Recently I also landed an internship with one of Boston’s favorite bloggers and interior designer. Leaving your comfort zone is hard but it can lead to great things!


This is a topic that’s been circling around the web for the past several months and I’ve taken it to heart. One of my daily struggles between my business, my Blog and other responsibilities is finding the time to do it all without working late into the night and neglecting my friends and family in the process. I’ve been trying out several methods to help work more efficiently such as setting time limits, batching tasks, and working on my most important or time sensitive projects earlier in the day rather than waiting until the late, lazy afternoon. Slowly, but surely I’m discovering what methods work best for me.


The other day my rambunctious three-year-old niece stopped what she was doing, leaned in close to my ear and whispered, “I love you, Auntie,” my heart melted. I know she loves me, she knows I love her but it took on a whole new meaning when she told me completely at random and unprovoked. Think of what a smile and courteous dialogue could mean to a harried salesperson or your local barista. Or what relief you can bring by assisting an elderly neighbor burdened by grocery bags up the stairs or down the hall. I am reminded of the saying, “Be kind, for everyone you meet is fighting a hard battle.” These little random acts of kindness often have the biggest emotional impact both for you and for those you’ve helped.


I’ll be perfectly candid, I’ve struggled with varying degrees of anxiety my entire life. I’ve had to learn, the hard way, to listen to my mind and take a little personal time everyday, to find a bit of inner peace after a crazy day. To breathe in the positive and breath out the negative. I find my daily yoga practices and monthly facials work best at slowing down my racing thoughts. It may seem like an extravagance to spend time or money on such activities but instead think of it as investing in yourself and your wellbeing. Without this you can’t be at your best professionally and personally.

Check out past DESIGN YOUR LIFE interviews.

biz ladies profile on design*sponge
April 25th, 2013     |    Business AdviceLife



During this kinda/sorta chaotic week, I haven’t had a chance to share some very exciting news: I’ve been profiled in Design*Sponge’s Biz Ladies series!

I deeply respect the Biz Ladies series and I recommended it to many of my business clients. It is a great resource for free, high quality business advice.

To find myself among the women and men profiled here feels pretty surreal.

I’m deeply grateful that I got to share the journey I’ve been on over the past fourteen years of entrepreneurship. As usual, I kept it real and shared the high and low points of the journey and have some practical advice for those starting out.

Thank you Grace and Stephanie for the chance to share my story!





{Things have been so hectic since I got back from San Francisco that I’m still catching up on everything. This also meant that yesterday I did not get the Wish I Knew Wednesday teaser posted like normal.}

This week today on Wish I Knew Wednesday, I will be focusing on dealing with poor business investments. Though it’s not often talked about, there are times in almost all businesses when we invest in business tools or programs that turn out to be a waste of time or money (often, both).

But there are silver linings to these investments. I’ll be sharing more about what to do if you find yourself in this situation in today’s email.


If you’d like to get the email, simply sign up by clicking on the image below. This email list is also where I announce upcoming workshops and other Business With Intention updates.

(If you have signed up for the Wish I Knew Wednesday newsletter, you will automatically get this email.)


the wise thing to do
April 24th, 2013     |    LifeQuotableThink About It



Contemplating major behavioral change or seeking the next steps in some area of your life?

This single question is remarkably insightful and practical.



san francisco workshop recap
April 23rd, 2013     |    Business Advice



Now that I’m back in Chicago, the workshops in San Francisco feel like a whirlwind!

As I’ve been prepping this recap it’s been nice to take a little trip back to the action and remember all the details.


I had so much fun in the Business with Intention workshop. We spent a lot of time focusing on the business purpose for each participant. We found new insights and opportunities for each person to take things to the next level.

In addition, the new With Intention Notebooks made their debut!


It was so great to see notes added to the beautiful workbooks created by Jackie of Believe Notes.


On Sunday, we had our Life with Intention workshop.


We had a great time clarifying what intention really means and there seemed to be quite a few ‘a-ha’ moments for each participant.


And when it came to running the show, Natalie Comstock of Natatlie Dressed and Casie M. of Skipping Scones did a fantastic job.

Natalie was our stylist/assistant for the weekend. Did you notice on her welcome table in the first picture that she included the workshop participants names in the framed welcome sign?

I’ve never seen a more clear communication of my brand: white, gold, coral, flowers, The Seven Habits of Highly Effective People, and The 4-Hour Workweek all represented.

Talk about above and beyond.


And then there was the food.

Amazing, delicious, and healthy food. The meals paired with the presentation really made the day feel like we were living in our own little Pinterest world.




Jen, my amazing Commander in Chief, outdid herself on the goodie bags this time around.


We are beyond thankful for the following small business owners for supporting the workshops:


Sarah of Parrot Design Studio shared stationery care packages and calendars (seen below).

Melissa of Melrose Street Custom Content gave each Business workshopper a complimentary content session to help them with their business website.

And Shannon of Simple Pursuits donated a note card that speaks to the intentional side of the workshop.


Jen of Jennie Claire made beautiful gold-filled necklaces for each participant as well. (I’ve been wearing mine almost every single day since.)


We also had these gorgeous candy colored leather notebooks from Angee of Sheic Journals. So cute and practical!


Linda of Ruby Red Design Studio gifted these adorable standing calendars.


And last but certainly not least we had a pouch filled with goodies from Alicia of Whimsey Box! (You can imagine my delight when I saw the gold and white washi tape.)


Now, it’s time to let some of the workshoppers share about their experience in their own words.


“The way Jess tells it, I only signed up for the Business With Intention workshop for the cute notebook. Here’s the thing–she’s right! When I saw the gorgeously designed workbooks on her website, they represented how I envision my business. I want to be the kind of self-assured, passionate entrepreneur who writes her fabulous ideas in a notebook like that.

I’ve made some pretty big mistakes with my business, and I’ve followed bad advice that put me in debt and made me hate the work I used to enjoy. During the workshop, Jess explained that those mistakes happened for a reason and I can learn from them and be of better service to my clients and myself. I was touched by her empathy, and I feel like I can forgive myself now.

The best part of the day (and there were a lot of good parts including the content, food, and ambiance) was the one-on-one attention I received. I’ve been to other business events where everyone gets the same broad information. Jess took the time to really understand my concerns with her unique way of seeing what truly motivates her clients (it’s kinda freaky!).

And my learning didn’t stop after the workshop. We were given exercises to deep dive into our businesses’ purposes and intentions. The workbook modules have me taking my big-picture ideas and breaking them down into actionable baby steps for today and the weeks and months to follow. You can’t find this stuff anywhere else, and believe me, I’ve looked.

The notebook alone is worth the cost of registration. Oh, and it’s super cute too. Thanks for everything, Jess!”

– Sage Grayson, Sage Grayson Coaching, Business with Intention workshop


“I came to the workshop looking for tools and directions for my life and those are exactly what I got.  Of course, a day away to focus on ME and my visions also was a treat.  Within the first thirty minutes, I knew I’d come to the right place.  The workshop felt like an emotional retreat for me.  Jess created such a welcoming, loving and excepting environment that it was easy for me to open up and be heard.   I was able to voice my concerns and together, we worked out solutions that felt right to me.  It was all in all a fantastic day!”

– Sunray, Life with Intention workshop


“I had such a great experience working with you and the other wonderful women yesterday! Not knowing what to expect, I decided to throw myself head first into the experience. Being honest with yourself can be a scary and somewhat difficult thing– but I felt nothing but supported and encouraged to speak my deepest truth and I’m all the better because of it. I feel confident moving forward to the next stages in life after developing a personal, realistic approach to my priorities. In fact, I am inspired to push even further! The Life with Intention workshop was exactly the jumpstart I needed in life and I cannot thank you enough for your compassion and advice.”

– Jenny W, Life with Intention workshop


“When I got the email from Jess’ assistant, Jen, telling me I was chosen as the stylist/assistant for the SF workshops, I was shocked, but also thrilled. Jen and I emailed back and forth leading up to the workshop discussing guidelines, my styling ideas, logistics, etc. Jen also put me in contact with Casie, the talented foodie for the SF workshops, so we could coordinate the meal setups. Jen made the whole process leading up to the workshops simple and stress-free.

Working the actual workshops was so much fun. Jess gave me and Casie both the freedom to execute our ideas as we wished. I wasn’t surprised to see how kind and fun Jess was is in real life. She has a light about her that just makes you want to be best friends with her.

Jess invited Casie and I to join in the workshop discussions whenever we had spare time away from our duties, which was really exciting for me as a long-time reader of Jess’ blog. The With Intention workshops inspired me and gave me more clarity than anything I’ve experienced. Jess really has a knack for helping people find their purpose, but she also makes sure to give you actionable steps you can take to move forward. She is the best listener and is really great at pealing back the layers and showing us that what we really want is already inside of us – a lot of times it’s just hiding under a bunch of crap. I left feeling refreshed and ready to move in the right direction rather than stressed about trying to carry out some massive, out of reach dream.”

– Natalie, Natalie Dressed, San Fran Stylist/Assistant

“Being chosen as the “With Intention Foodie” was the best experience – Jess really gave me the strength to run my own show for the event. Even though I’m an amateur, she had confidence in me and let me contribute to her already inspiring workshop.  I believe Jess is a great listener and a great innovator, someone you’d want to have as friend and that is really telling during these workshops.  The attendees really need to open up so Jess can do her best ‘work’ and she completely enables each individual to do so.  I truly had a great experience and would do it again.  Thank you, Jess!”

– Casie M, Skipping Scones, San Fran Foodie


Thank you, thank you to Jen, Natalie, Casie, and the workshoppers for supporting me during the awesome weekend. I’m beyond grateful to get to work with you and serve you.

And for those interested in the Austin Life and Business workshops in June, is exactly one spot left in each workshop!


photos by myself and Natalie

Jen here, and it’s Friday! How was your week? Any big plans for the weekend?

Today, I have a guest that I’m truly looking forward to introducing you to. Her name is Liz and she is the blogger behind Grey and Scout. I found her blog, loved it, clicked on her twitter, and we eventually started chatting and have since become twitter-friends (lucky me).

Liz has a witty sense of humor that will make you laugh, she is open and honest about good and bad days (that we all have) and her blog is full of beautiful images that are drool-worthy. Liz is a blogger with impeccable taste and  is amazingly talented at home styling. When you visit her blog, you will fall in love with her house tour, and you will want all her favorite interior pieces. It is hard not to be inspired by all the things that Liz provides, so needles to say, I’ve been excited to see how she designs her life with intention.



I went through a period of time when I just could not fall asleep. And if I did manage to drift off for a few minutes, some electronic device was near to remind me of all things I had on my to do list (and my to do list is ironically what was keeping me awake in the first place!) I’d had it. If it’s capable of making a noise, it’s gotta go! No more electronics on my nightstand. I replaced my iPad, laptop, cell phone and a billion chargers with soothing scented candles, fresh flowers, and good reads. I suffered from withdraw symptoms of sorts for a few nights, but very quickly discovered that all of the work, emails, instagram photos and new pins would be there the next day. I’m two months into my over-wired rehab and have been sleepin’ like a little baby!


During office days, I read blogs, websites and emails all day. I proofread, write and re-write. I sit down at my desk at 8am, and for some unknown reason it is shocking when I look up and it’s 6 o’clock! While emails and blogging are a part of my job, and I love composing posts, there are days I feel like the content I read online is singular. I found myself craving more. I started a small ‘movement’ to combine my days with all the online goodies and some good ol’ fashioned, tangible page turnin’. First on the list, finally finishing Diane Keaton’s book ‘Then Again’ and Mindy Kaling’s ‘Is Everyone Hanging Out Without Me.’ You know, because everyone who’s trying to find time to read should start with two books.


Clearly, I’ve got a theme goin’ on…less virtual, more real. It has taken me a long time to embrace the quiet moments in my life. To be still and really take in my surroundings. Not just hear, but really listen to someone without constantly checking my phone for new emails. To pour a glass of wine, sit down with my husband and have a conversation without the TV as background noise. My goal is to truly see, feel, and live every moment, good or bad.


Big or small, celebrate the moments that make you smile. For me it’s completing a styling project, partaking in an especially rewarding day volunteering, not forgetting to fill the coffee maker with water, waking up on the right side of the bed (seriously, it’s the small things)…celebrate all the moments that make you feel good. No more saving the bubbly for “something big.” Big is now, and now is what’s most important. Now is today and today is worth celebrating!


Keeping true to me, my beliefs, my thoughts, my style as a blogger and writer is easier said than done sometimes. I see or read something and it can sometimes be difficult to stay the course and remain true to my vision. I’m the first to admit that when I see someone else’s amazing blog or hear that someone came up with a crazy awesome idea, I sometimes feel like I need to rethink everything. But becoming more confidant in my vision, embracing my triumphs and my mistakes, not comparing others’ successes to my work, and staying committed to my path, I can be truly happy for myself and for others.

Check out past DESIGN YOUR LIFE interviews.

focus and simplicity
April 18th, 2013     |    Business AdviceLifeQuotableThink About It



This week I have been hustling with my regular workload while preparing for the San Francisco Life and Business with Intention workshops this weekend.

Since today is the last day I have to get everything settled until next Tuesday, I have quite a lot to jam into the few hours before and after my client sessions this afternoon.

Which means I’m taking Mr. Job’s advice and focusing on the top priorities and keeping things simple.


the purpose-based business manifesto
April 17th, 2013     |    Business Advice



After working with hundreds of small business owners across the country (and Canada and Mexico, too!) grow businesses with intention over the past two years, I have come to deeply understand that designing a business “with intention” is only part of the equation.

In fact, it’s the second part of the equation.

The first part of the equation, if ignored, generally leads to disappointing sales and a sense of frustration. Of not feeling “special enough” in the eyes of the customer or the entrepreneur (sometimes, both).

A truly meaningful and successful business must be based on purpose and then grown with intention.

This is so essential that I’ve now redesigned my entire business arm of my career to helping business owners answer the first and second part of this equation.

Below is my manifesto for this often missing link.


The Purpose-Based Business Manifesto


We live in a wonderful time.

A time where it is easier than ever to start and grow small – and large – businesses with the help of technology and the internet.

A time where people no longer believe “getting by” is an acceptable way to live.

We want to thrive.

We want more from our lives and careers – in very individualized ways.

This desire to do something that matters and pursue our passions has led to an explosion of new businesses. Often, these businesses are creative with a strong online presence.

In fact, women owned businesses in the US are up 54% in the past 15 years.

Indeed, it is a wonderful time.

But with this business boom, the creative business industries have gone from lean to bustling.

This influx of peers has resulted in a feeling of over-saturation for some.

To thrive in the creative world, we can no longer simply call ourselves “stationery designers,” “copywriters,” or “health coaches.”

Those are crowded spaces with many claiming the same.

Rather, we must lean deeper into our hearts, talents, and experiences and draw upon our own unique value proposition to stand out and differentiate ourselves within our industry.

We must draw products and services from our purpose, not the other way around.

From a place of clear, authentic purpose we can find higher value (bigger profits), service (more fulfillment), and our ideal clients (people who desire exactly what we have to offer).

Our branding, marketing, and social media actions become direct, clear, and unique when we let our purpose direct our steps.

Though it may seem daunting to try to define a purpose for your business, it is far from difficult.

In fact, I’m here to help you do just that.














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