Best & Worst: My Former Clients & Employees


Photo Credit: Sean Hayse

Have you ever done the “rose and thorn” activity? It is sometimes called “peak and pit” or “high and low.” It’s one of my favorites to do around the dining room table. The activity goes like this: each person gets a turn sharing the best part of their day and the worst part of their day. My favorite thing to happen during this activity is the realization that you didn’t have a “worst part” of your day. This is also a good activity to do after milestone events like at New Year’s, the end of the school year, or the end of a vacation. Today, I am going to share the best and worst moments with my former clients and employees. I learned many things along my entrepreneurial journey and I am finally ready to share more about what transpired behind the scenes. Let me be clear, my hope today is not to rile anyone up, but rather to encourage other entrepreneurs who may be experiencing “thorns” at this time.


Once upon a time, I had a client who came to me as a referral. I was told this client had some sort of social anxiety and to forgive any awkwardness that might happen in the beginning, as we got to know each other. I have anxiety myself so at the time this was not a red flag. Upon sending the proposal, the client asked to pay the entire contract amount upfront vs monthly.  I had never had that request before, but I saw nothing wrong with it and proceeded with the contract. About a month or so into our time working together this client showed up at our office. This client proceeded to question one of my staffers on their account. However, in the beginning of new contracts I worked the accounts myself before handing them over to my staffers, so the staffer being questioned had no information for the client. This client then asked my staffer for their money back. Again, not being in the position to oblige this request, my staffer was left to take the abuse. I was able to talk to the client later that day and explain our processes, but this began a cycle of rage and repeat. Eventually, we did end up terminating the contract and issuing a refund. It was just too toxic of a relationship to move forward. Marketing is a creative process and if your marketing team isn’t feeling safe in the relationship do not expect great results. 

As horrible as that experience was, the lessons I learned and the appreciation I developed for my other clients was invaluable. Speaking of other clients, my best client was one of my first clients. They took a chance on me, grew alongside me, taught me not only business lessons but life lessons, and I am forever grateful. The best clients become part of your team and inevitably part of your family. 


Once upon another time, I had an employee who I was super excited about. Everything on their resume and in their interview was spot on. Imagine my heartbreak when on their second day of work a Facebook post went out bashing their new life situation. It wasn’t explicitly about our office, but feelings were definitely hurt. Nonetheless, we continued forward with a laundry list of diva-like requests for months. The last straw came when I asked this employee to take pictures for a client’s website. It was not  uncommon that we needed photos for marketing purposes. Myself and other staffers were very accustomed to this type of request. This employee however was not willing to do the task. I re-assigned the task and asked the employee to take the day off so we could all cool off. I proceeded to receive a barrage of emails over that next night and day that ultimately led to my letting the employee go. Looking back, there were so many red flags that any human resources professional would have caught.

The next time I needed employees my interview process was much more robust and included input from the entire team. Although none will replace my first ever hire, my next few hires were absolutely amazing. The staffers I had at the end of my agency days are some of the most inspiring, creative, driven, mature, interesting, and fun people I’ve ever had the pleasure to know. From time to time I catch glimpses of their current marketing work and I could not be more proud to have worked with them.


For all of the planning that goes into entrepreneurship, it will be the moments you never saw coming that will knock you off your feet and ultimately define you. As much as it will feel like a failure, I promise that as long as you learn even just one thing it will all be worth it. Continue forward on your mission, try to enjoy every peak and pit along the way. For me, having a fresh set of eyes and ears on a situation usually helped immensely. If you ever need someone to talk to about your entrepreneurial adventures, feel free to contact me any time!

One thought on “Best & Worst: My Former Clients & Employees

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.