We live in a digital age where people’s highlight reels are regularly flaunted on social media.

Pictures of happy families, perfectly manicured yards, gorgeously styled homes, and deceivingly trim physiques take up prime real estate on our iPhones.

And while it can be all too easy to assume people really are living the good life 24/7/365, we need to remember that people only show what they want the world to see.

Business is no different.

You might see entrepreneurs in the online space and think they fell into the success they’re currently experiencing as you scroll through countless posts of multi-million dollar launches, luxurious vacations, and groundbreaking sales numbers. 

Understandably, the images, stories, and videos you encounter might lead you to think that somehow these business owners and entrepreneurs were gifted a magic recipe that made all their business hopes and dreams come true. 

And for 99.9% of us (except for maybe the likes of Kim K ?!), that journey is far from glamorous. 

It often involves a lot of figurative blood as well as literal sweat and tears. 

But despite the fact that the majority of successful businesses require substantial effort to not only get up and running but to maintain their momentum…

…too often we see the “after” of their entrepreneurial makeover without understanding what the “before” looked like. 

In my opinion, this is a HUGE disservice (not to mention downright discouraging) to new entrepreneurs who are embarking on their own unique entrepreneurial journey for the first time. 

So, in the name of full transparency (something I am very passionate about in business), the purpose of this blog is to pull back the curtain and reveal a bit about the not-so-linear path that took me from the corporate world, to stay-at-home mom, to full-time creative entrepreneur. 

My hope is that my journey inspires you to take risks, get messy, and follow your passions as a creative business owner!

Version 1.0 of my business coaching program for creatives

The first version of my business coaching program happened completely by accident. 

Maybe you can relate as a creative entrepreneur.

Let’s take a quick trip down memory lane. 

Up until 2014, I had spent the previous 6 years working for a design firm in NYC. I left the company when I moved out of state to get married and start my family.

And then the phone call came.

A few months after my leave, my former boss reached out with a proposition. He knew I wasn’t able to return to the firm, but he had noticed a big void at the company since I’d left– specifically in the area of coaching.

He asked if I would be open to doing some freelance consulting work and wondered if I’d be willing to coach some of his employees, and even him for a bit. The company was evolving and he was looking for some support and guidance to help his team grow, adapt, and take on new challenges.⁣ 

I agreed, and never looked back!

Coaching work had always sparked something in me, but up until this point, I had never coached exclusively. Nor did I have a fleshed-out program.

This was the first time I was formally hired to coach. Like many “accidental entrepreneurs,” I had to rush to figure out how to invoice and organize all the “fun” business-y stuff! 

While I didn’t have a lot of experience running my own business (yet), what I did have was a ton of experience helping companies and creative individuals thrive from a systems and ops standpoint and a knack for the logistics side of creative business. 

And once I tapped into that, my passions soared!

This opportunity quickly validated my love for  helping creative business owners transition from surviving to thriving. Watching them grow in confidence and skill and witnessing them reach new heights became my absolute favorite.⁣

This freelance coaching experience helped me build my confidence as I dove head first into the “deep end,” of entrepreneurship.

And while it all felt new and exciting, the reality is, I had already been coaching for a number of years (probably 5 years) before that. 

So what was different about THIS coaching opportunity? 

In the past, coaching felt more casual, and not so much like a real business or a formal job.

That’s because “sessions” often took place over coffee dates, on quick phone calls after work, while helping fellow creatives brainstorm ideas at networking events, or during quick water-cooler-esque chats with colleagues before meetings in the conference room of that NYC design firm.

In contrast, being hired – and paid – to coach my former boss and his team felt a bit more “legit.” While I was still taking these calls on my commute home from my new 9-5, the experience planted a seed that this work could be so much more than just a side hustle…

Fast forward to motherhood and the birth of my daughter. 

I decided to leave my 9-5 job, but I held onto coaching for my former boss’ company! As I gained more and more experience, my coaching process evolved. 

These sessions remained completely customized to the person I was coaching and their most pressing issues, but I started to build consistent frameworks to support things like… 

• short and long term goal setting
• logging action items
• celebrating wins and tracking challenges
• crafting and implementing meaningful plans

This continued until my second child was born. 

I took some time away from FORMALLY coaching, but never actually stopped altogether. 

I found myself coaching here and there in any pockets of time I found available to me– clearly a sign that I felt called to do this work. 

It was the kind of work that never quite felt like work at all…

Then, I had a bit of an epiphany. 

In late 2019 I heard myself say something to one of the creatives I was having a conversation with. 

I said,  

“You need to start treating your business like a real business”. 

Now…

this is something I said to pretty much EVERY creative I was informally coaching at that point

…but this time it resonated differently.

I realized it was time I took my own advice.

What happened next

And so, I decided to practice what I’d been preaching and began to formalize my coaching business.

Finally!

I filed an LLC and joined an online community and course for support to get the ball rolling (yup – even coaches need coaches sometimes!).  These foundational pieces helped me to nail down my first formal coaching packages.

I felt ready to officially bring Erin Cantwell Co. out and into the world!

I launched my business in February 2020.

And I probably don’t need to tell you what happened next. 

COVID hit. 

The world spiraled. 

Sure, I could have seen this as a huge misfortune. 

Poor timing. 

Bad luck.

Not meant to be. 

And yeah, I felt sorry for myself from time to time. But instead of letting the circumstances crush me, I let them fuel me. 

→ I pivoted my business and decided to help creatives leverage their creative talents to help others in the early days of COVID.

→ This evolved into a weeklong virtual workshop/challenge to help furloughed or laid-off graphic designers turn their freelance business into a thriving business.

→ And then, I unveiled my very first official 1:1 coaching program as a LEGIT business owner (even though I was always legit, I just had to see it that way and truly believe it!)

The Version 1.0 Coaching Package Breakdown

Now, let’s dig into the meat and potatoes of it all!

I’m not here to give you wishy-washy information. 

So here are the facts. 

THIS is exactly what the initial specs of my coaching offer looked like with my launch pricing:

I priced my coaching package at $500 but offered a special promotional price of $375 when I first launched.

The offer Included:

• 4 one-hour weekly coaching sessions via Zoom call (at the time I valued this at $600)
• Tools to help my clients develop and strengthen their business (as needed)
• List of supplemental resources (as needed)
• Unlimited access to me via email during the duration of coaching

And as a bonus, I threw in 2 FREE sessions. 

CRAZY.

In fact, many of the tools and resources I offered in this initial package are things I still use to this day (although they’ve since been updated and refined many times over).

COO Tip: My Time Audit Tool is one of those resources I’ve developed and perfected over the years. It’s yours for FREE if you click here.

How my coaching programs have evolved

Quite a few other things changed about my coaching programs over time. Often this involved trial and error to figure out what resonated and what didn’t. But more importantly, the better I understood my clients’ challenges and shared experiences, the better I could tailor my programs to fit their needs. 

3 things stand out to me most when I consider how my coaching programs have evolved from version 1.0 to 2.0 and beyond…

#1 The Cadence

The cadence of my coaching has changed significantly. While I started with a 1-month coaching program, I now start EVERYONE on a minimum 3-month package. 

Why?

Because I saw over and over again that 1 month wasn’t quite enough time to do the real work and see the transformational effects that coaching can have. 

The longer timeline allows me and my clients to… 

• dig deeper
• get to the root of problems 
• try out different strategies

Plus, it lets me support my clients as they implement the strategies instead of leaving them to fend for themselves. And…as they implement, new challenges inevitably pop up so this continued access to me lets me support them in real-time!

#2 Zoom Support Flexibility

One of the first changes I made when it came to coaching sessions was switching to 3 Zoom calls per month. This may seem counterintuitive, but sometimes less is more!

This change allowed me to build in 1 week for implementation rather than meeting with my clients every single week. 

Both my clients and I benefited from this arrangement!

I found this helped build confidence and autonomy in my clients. The more they were able to flex their muscles on their own, the less they relied on me each session. This worked like training wheels. Plus, the one “off week” gave them more structured implementation time to put their plans into action. Because what we work on ONLY works if it’s implemented. I saw a significant increase in follow-through and strategy effectiveness. 

#3 Diverse Coaching Options

Lastly, as time passed, I expanded my offers beyond the introductory package.  

I developed new ways to work together beyond those initial 3 months. Some of my clients wanted the same level of support moving forward. On the other hand, other clients felt they still needed support but not as much because we had built a solid foundation for them.

So I responded by creating 2 additional coaching packages that clients could “graduate” into:

The bi-weekly package and the once-per-month package. 

Today, these more customizable options allow me to still support clients past the initial 3-month package, but at the level they need. Plus, it gives them comfort knowing I’m always just a Voxer or an email away, even if our sessions are more spaced out.

The Ever-Evolving Creative Business 

To this day I continue to hit roadblocks, overcome challenges, and innovate new ways to do things in my business as an outsourced COO and business coach for creatives. 

I’ll be totally honest. Despite my best efforts I’ve…

• Set expectations and timelines that don’t always work out the way I’d hoped. 
• Dropped the ball on projects that are important to me.
• Overbooked myself and struggled to maintain boundaries.

Because at the end of the day, while I am the CEO of my company, I am also HUMAN which means I will inevitably stumble and fall. 

It also means I will pick myself up, dust myself off, and come back stronger, not in spite of, but because of any setbacks that come my way. 

This journey is not linear and any coaching program that promises you a clean-cut, step-by-step plan is simply false. 

Your business is one-of-kind and with that will come unique challenges, offers, and successes! 

And while you can’t possibly anticipate every outcome, you can move through entrepreneurship with grace, knowing that both the ups and the downs are part of this beautifully messy experience!

Gain Clarity On Your Next Steps

If I can support you as you overcome your most pressing business obstacles, please do not hesitate to reach out. Even if you aren’t at the point where you can commit to a full coaching package, I offer Clarity Calls to help you break through your toughest issue and finally get clarity on your next steps. Click here to learn more about these 90-minute intensives.