The Wild Ride Called Entrepreneurship

Omg.  My business just crossed the 15 year mark.

Here’s a synopsis about wild ride called entrepreneurship:

I’ve been in business since 2004 …. and over these 15+ years my business has had many “brands”, offered many different programs, and has persevered countless evolutions. Countless!


Ok, so, right out of the gates, I messed up. I named my business “Transition Coaching & Event Planning”. So wrong. Here are a few of the *many* reasons this was “off brand”:

1.) I kept getting phone calls from people asking me to plan their wedding. lol. Having to explain time and again that it’s a coaching company and not a wedding planning company was my first clue.

2.) I soon realized that ‘transition’ really isn’t fun or something that people are eager to sign up for.

3.) Together with the few clients who graciously overlooked my terrible branding and decided to work with me, we were having *far too much fun* for transition to remain the focus point and the “brand” of the work I do.

4.) I came to realize that I inevitably found my way to asking my clients the same question, “What’s the dream here?” and this sent us in a whole new and wonderful direction.


After asking for guidance about what my business name should be, I woke up in the middle of the night knowing exactly what to change it to: “Create Your Life!”. It felt right. This sparked my business taking on new life, with inspired idea after inspired idea.

I wrote a curriculum for a 5-week Dream Circle group program. I networked my butt off, telling anyone who would listen about my work and my business. Clients who were ready to dream their life bigger and create their life to be something they couldn’t wait to get up and out of bed for in the morning, were becoming my clients. In 2008, I started hosting a special annual event that put me “on the map”: The Dream Party. ‘Come as you aspire to be’ was the tagline, and for 5 consecutive years, 100 or so people came to this weird and wonderful event, dressed in ways that represented their 5-years-from-then self.

They crossed over ‘the footbridge to the future’, they acted and inter-acted as if it was 5 years into the future, celebrating all the dreams that had come true in their life. They wrote letters to themselves in the shed-sized Time Machine art installation that I hired some RISD students to build for me (the first year, the paint was still drying as guests arrived) …. And 1-year later I mailed attendees their unopened self-addressed letter along with an invitation to the next Dream Party, of course. 😉

The Dream Circle evolved too …. into what is to this day my signature program: The Dream Acceleration Program, a comprehensive online program that I couldn’t be more proud of.

Create Your Life! was my growing baby. I was delighted by it. A traveler at heart, knowing that I couldn’t live my entire life in one location, I longed to do meaningful work while also having the freedom to travel when and where I please. By design, I created my business to be location-independent, working with clients remotely – even if they lived in the same city! Back then, Smartphones weren’t in every pocket, the Internet was not accessible everywhere, Internet marketing wasn’t mainstream, and the term ‘digital nomad’ had not even been coined yet. Thanks to the virtual nature of my work, and my growing virtual team, Create Your Life! was serving clients from as far as Spain, Israel, New Zealand, Canada, Costa Rica, and all across the US. A lot changed in my life over this period of time, but my work was consistent and an aligned extension of who I was – and who I was becoming.


The short story is that while I kept at it and never for one moment adored my clients any less, I started to feel like something wasn’t quite right. Like something that used to fit me perfectly was no longer exactly right. Like I was outgrowing myself. Ever feel like you’ve outgrown yourself?

It’s important to note here that, in 2012, I completed a unique Masters degree program: Holistic Leadership. I credit this program with sparking several new ideas within me, many of which I integrated into my coaching work and into how I facilitate my programs and how I train others to do so. This Holistic Leadership degree taught me new and expansive models, perspective, and approaches to powerful leadership — the kind of leadership that people are eager to follow — and it watered many seeds within me. I wasn’t looking for a Masters degree program, but I happened upon it, by no coincidence.

While MA behind my name is great and all … as a devoted entrepreneur, I didn’t have any expectations or intentions of this MA being a career-maker in a resume-kind-of-way. I found the coursework so enriching that I stayed with it, inching my way through the program. At the end, I felt no need to attend the graduation ceremonies, but my mom insisted – she wanted to be there. So, when they called my name, I walked the stage to receive my diploma and I was truly caught off guard by how emotional crossing that stage was for me, a significance that went far deeper than any piece of paper. It represented a personal threshold.  (Retrospect is often 20-20, and I see now how this threshold seeded my 2013-2015 “it doesn’t quite fit anymore” phase.)


By 2014, my soul was really itching for something new. One way I scratched the itch was to move – from lil’ Rhody (a place I love and always will) to the DC area. A wise friend of mine who witnessed me on the cusp of this decision said, “Tara – there’s no wrong answer. You love Rhode Island, and you can stay. Or, you can move to a new place.” She likened me to a plant: “You’re a perfectly good plant in a perfectly good pot. But if you repot, you’ll grow.” I decided to repot, and in 2015 I moved to just outside DC.

I danced like crazy. (If you don’t know this about me already, I love salsa dancing.) Unlike ‘lil Rhody where there’s typically only one salsa night each week … in DC, I could dance every night if I wanted to. And I wanted to about 4 out of 7 nights. 🙂

I met some wonderful people (one of whom I live with now) — but DC didn’t feel like “my place”. My nomad soul called. While the international vibe of DC really spoke to my nomadic soul, the vibe of politics infused so much (too much) of life there. Generally speaking, my experience was that the culture is such that people live more in their head and less in their heart and body (than I want to at least). It wasn’t my forever home. As a nomadic soul, no where really is. 🙂 But it turns out the the DC area wasn’t my “more than 2.5 years home”. It was time to go.  

While in DC, in addition to Create Your Life!, I launched a short-lived off-shoot business that I named Nomadic Leaders with the vision of offering a coaching program for laptop leaders – something that would bring travel, community, and coaching together. But, I having two brands: Create Your Life! AND Nomadic Leaders quickly became daunting and felt disjointed. My energy felt split and neither one was getting the attention it deserved.

In 2017, along with my boyfriend Carl, I finally made the leap into nomadic living. We now live full-time in an RV, working from the road, salsa dancing along the way, and exploring each state at our own pace: one of the best decisions I’ve ever made. We now offer a special program Nomadic Living 101 and speak at RV Shows about the nomadic RV lifestyle and help others do it too!  🙂

2018 – present

In 2018, it became clear that yet another re-brand was needed. After all this time, I finally realized: I am the brand. I am the common denominator. It became abundantly clear that Create Your Life! & Nomadic Leaders needed one home: in me, Tara Sage.

Ugh. (was my initial thought)

I sighed.

I didn’t want to have to re-create, yet again.

I resisted it for about 48 hours.

And then, the clarity of HOW to bring the two together into one cohesive, it-can-grow-as-I-grow, I can pull together the best aspects of each into one home-of-awesome that will be better than the two …. followed. I saw that I’d be better able to show up fully in service, because my energy won’t be “split” and it’ll always be a just right fit because …. I am the business: Tara Sage, Inc. was born.

Amen. ***(If you read this far, please comment below, if for no other reason than so I can bow to you.)

And with the launch of the all-in-one brand, followed the launch of the all-in-one website:

Ever feel like YOU’ve outgrown yourself? If so, let’s chat.  I know a thing or two about that and how to create your life and business from a place of authenticity, service, and truth. 🙂 

So check out the new site and pass it along to someone you know that you think would be well served by it/me.  

And here’s to another 15 years!


Tara Sage