How I Successfully Pretended to Run a Business for the Last 18 Months


It’s time to get something off my chest. For the past year and a half, I’ve been pretending to run a business. I’ve been posting about my “business” on Facebook, and Instagram, and LinkedIn. You’ve all been asking me how my “business” is going. I’ve been blogging about the joys and challenges of running this new “business”. Well guess what… 

It’s all been a lie. 

At least in some sense. I’ve been thinking more about businesses lately (real businesses), and how I really would like to start and run one one day. But I don’t yet. Not in the literal sense. 

Let me explain.

What I do isn’t running a business. I’ve created an avenue for self employment. I have developed a word-of-mouth supported network from which people can hire me to do a job for them (specifically, write resumes). For every paycheck I earn, I take on a certain amount of work I need to do. 

It’s not scalable, and therefore in my eyes… not a business. 

My Dream

  • I would love to own a business.

  • I would love to build a system in which not every dollar earned comes from my time.

  • I would love to have a team of staff who are working my system with me.

  • I would love to advertise my services without fear of running out of time to serve clients. 

And that’s what I’m working on!

How I Plan to Build a “Real Business”

I’ve already taken a couple of key steps in moving away from the “more money = more time working” model. 

1. I created two video courses hosted on (which you can check out here with a free trial). 

I created the first course in February “How to Write a Winning Resume and Land Your Dream Job” (perhaps a little too generic and that’s why it had slow uptake) and the second one in June “How to Write a Marketing Resume and Cover Letter (downloadable templates included)” which has been slightly more fruitful. The third is on it’s way (focused on the Sales profession). 

I haven’t ever advertised these and I’m not sure why. I guess I’m not sure anyone would want them or find them useful. A bit of self-doubt there, but hey, I’m telling you now. 

2. I hired a writer!

One of my best friends when I was living in Florida, Rob Keever, worked at my University Career Center, and because he’s also a hardcore NBA fan, we really hit it off. Rob’s got 8 years’ experience in resume writing and I’m so grateful to have him on my team. 

Now, whenever I have a few too many clients reach out at the same time (which is an awesome problem to have), Rob will help by connecting with the client and writing a first draft of the documents for me to finalize in exchange for a percentage of the client’s fee. 

Bringing in Rob has done three major things for me that make me optimistic that I can transform this self-employment situation into a real life business

  1. It has given me the confidence that I can handle more clients, which has allowed me to start promoting myself again. 

  2. It has brought back a bit of that team feeling that I get from my day job where I get to collaborate and delegate (my favourite parts of that job).

  3. It has freed up some of my time for business development (such as blogging).

So thank you to Rob, and welcome to the team!

What’s Next: A Look at my Cold-Hard Numbers

Since I launched, I have served 88 clients (plus we three more scheduled for this week), and it took me 19 months. For the sake of simple math, let’s say I have a strong end of the summer and hit 100 clients in 20 months. That’s an average of 5 clients per month. 

I want to do better. 

What I’m doing has really helped a lot of people (check out my freakin’ awesome testimonials page), and I want to help more people! I just don’t think I’ve quite got the model to do it yet.

Sure, I can bring on more Rob’s (although there’s only one Rob: a man who somehow manages to be so well informed on life and yet have such a poor grasp on the NBA landscape (I know you’re reading this, buddy, and I await your counter argument in the comments)) but even with Rob’s support, there is still a time commitment with every new client (albeit smaller). 

My Big Idea… (I want your feedback on this)

I think my path for true scalability is in education. Mass digital education. I’ve been testing my luck with the Skillshare Courses, but my big idea is much more than a video course. It’s an all-inclusive job search walk-through that will helps users with:

  • resume writing

  • cover letter writing

  • LinkedIn optimization

  • interview prep

  • networking

  • overall job search strategy

  • And more…

I want to include video tutorials, templates, worksheets, and support groups to help share my tested methods and formulas with a much larger audience. 

To test this idea, I’m currently working through some activities I found in a book called “Will it Fly?” by my new one-way online business mentor, Pat Flynn (we’ve never met but he’s totally amazing and the best resource for online entrepreneurs I have found in my three years of searching). 

As I work through the steps in the book, I’ll update you with more details but for now, I’m optimistic about how this could help me scale my business out to help more people :) 

If you have any thoughts on this large-scale digital education idea, I would love to read your comments :)