I loved the freelancer life. From 2004 to 2009, I took projects that I liked and that would challenge me. I experienced a ton of different industries and leadership styles. I got to travel the world!

As a freelancer I have: 

  • Masterminded a popup shop long before social media existed
  • Designed a handbag collection and sourced production for it in Italy
  • Sold a variety of contemporary and luxury clothing/accessories
  • Assisted the coaching team of a high profile politician
  • Written a style column for a newspaper
  • Crafted online marketing and copywriting for a natural health brand
  • Created the PR plan and product line for a hot new young adult author 
  • Styled the wardrobes for an entire family
  • Consulted on the UX for a coaching dotcom
Sometimes I have to keep reminding myself of this as I grow. 

Sometimes I have to keep reminding myself of this as I grow. 

When I look back on my path, I realize that what looks like a a lot of randomness was actually a series of learning experiences that still informs my work today. The apparent randomness suited my life and working style (I’m a sprinter) at the time and I have zero regrets about it.

Now that I’m older, I see that being a freelancer is very different from running a business.

The biggest change, aside from keeping separate bank accounts for business and personal spends, has been changing my mindset. 

As a freelancer, my income was pretty much directly proportional to the time I spent working. The more I worked, the more I made. In some instances, I charged a premium for that work, but generating revenue still required my presence and input.

For me, running a business means creating IP and products that don’t require my direct input. The business is scalable and has intrinsic value even if I’m no longer a part of it. 

Until very recently, I didn’t really want to create a business. I liked my lifestyle, thank you very much. In good years I could earn multiple six figures and even when I don’t work that much, I am still doing well by most people’s standards: I don’t have to go to an office, I work with clients I like, doing work I enjoy. 

Not so bad! 

In 2010, I started doing corporate training and consulting. It was very customized for my clients and I didn’t see how I could possibly train someone else to do that same work. Still, I kept doing it and figured that the repeatable methods and frameworks would make themselves apparent. 

It’s taken some years, but now I have a vision for the training and consulting company that I’ve been slowly creating. 

Then moving back to New York City, getting married and having a baby all had a major impact on my decision to re-dedicate myself to building my business as a company with intrinsic value. 

Before, I was scared of the idea of employees and even did a lot of work myself (work that I could easily farm out). Now, I see that if I continue to see myself as an island, I’ll limit my own creative (and financial) potential.

So, my five year plan is about corporate and consumer trainings. Yes they might be my IP and personality-driven, but I’m working on a couple of trainings that I’ll be able to scale by bringing on new trainers. 

This is a different model from the solo practitioner consultant route that had been my goal for a long time and it’s a change I’ve decided to make since having a family. 

I want more time with my baby and hubs, less time delivering trainings and I have some financial goals that require scale. 

In some ways I miss the freelancer life- the unexpectedness of it, the novelty of a wide variety of projects. 

But building a business is more fun and more lucrative, if a bit more challenging for me as it requires a consistency that until now I haven’t had to institutionalize in my business.

A lot of solo practitioners call themselves CEOs (I now prefer the term managing partner), but now I’m actually putting on that CEO hat…and it feels good! 


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