Here Comes Trouble

A woman climbing over a fence.

At a certain point, every business owner will see his or her share of trouble. Trouble, like a color-morphing chameleon, takes many forms: a severed relationship, a project misstep, or a new business loss, among other things. Some of these challenges have the potential for wholesale destruction, putting the entire business at risk. Other situations will be less devastating. Looking back, Perhaps it is the way we choose to handle these difficult situations that gives us control over them.

Here are a few stories of challenges I’ve faced since launching my business in 2014, and how I made it through each situation, a little wiser and more or less in tact.

Troublesome Situation #1: Undervaluing my services

Back in the beginning, I struggled to make the shift to project-based (also known as value-based) pricing, having worked in the agency world, where time sheets were the norm. More than that, and for too many reasons to list in this article, I was afraid to ask for what I deserved.

What I’ve learned from this situation is that when I value my services appropriately, asking for fair and equitable compensation, I’m almost always offered a chair around the table with “right sized” partners and clients. ​Properly designed estimates help me sift out those projects that are too big or too small. My most rewarding client relationships happen when I value my expertise appropriately.

Troublesome Situation #2: Vetting vendor partnerships

My business is no more than the sum of all its parts. I don’t aspire to be a 100-person company, but I hope to grow to between 5 and 10 employees at some point. When a business is very small, like mine, every person that I bring onto my team, whether they are full-time staff or vendor partners, needs to be carefully vetted. Ideally, all the vendors I bring into my universe will share my attention to detail, my willingness to deliver more than expected, my work ethic.

Unfortunately, that’s not always the case. ​Having limited internal resources means my small team and I wear multiple hats. It may sound like a lame excuse, but finding the time to investigate partner vendors can be a challenge. A few times, in a pinch, I’ve hired vendors on face value, without doing the necessary due diligence to dig into their experience more thoroughly. Needless to say, these vendor relationships usually don’t last.

What I’ve learned is that there’s no substitute for checking references, digging into a vendor’s background, talking to people who have worked with them in the past. Certainly, this takes precious energy out of a busy week, but the return on this time investment is worth its weight in gold. Before hiring my most recent digital vendor, I spoke to three references and then handed them a small project to test the waters before going all-in. It was well worth it!

Troublesome Situation #3: Too many eggs in one basket

Yes, it’s a cliché, but cliché’s exist because they are mostly true. Let’s face it, new business is an arduous, ego-draining, never-ending effort. Keeping up the necessary energy level to be fresh and ready for a pitch or even to do the grueling backend work involved in nurturing new biz leads is a daunting task. Add this responsibility to the top of your typical day-to-day activities and you’ve got a full plate. I understand how easy it is to get comfortable with a few clients and not do the work to keep feeding the new business pipeline.

Two years ago, I had a big account that demanded my constant attention. They paid their bills in a timely fashion and I quickly got used to responding to their every whim. I did this at the expense of new business, in effect ignoring that little voice inside my head telling me that I shouldn’t be so complacent. Then it happened. My big client laid off most of its internal marketing staff, rendering me an indirect casualty. Within a month, the account was gone and I had to pedal pretty fast to catch up on my long-neglected new business efforts.

What I learned from this troublesome situation was that I should never rely too heavily on one client relationship, putting aside the health and well-being of my company, even when I’m being paid well. Relationship longevity is ideal, but not always the norm. My company deserves the same love I give my clients in order for it to grow and thrive.

​I hope that by recounting some of these real-life, troublesome situations I might save others from making the same mistakes. Even at this stage of my career, I still consider myself to be a work in progress, a life-long learner, and someone working to be a better boss and co-worker. Please share your stories of “trouble” along with your solutions in the comments below.

Anne Richardson

Anne Richardson is the owner and media director of Richardson Media Group, an agency specializing in media planning and buying, advertising campaign management, and SEO.


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Anne outside the door of the Richardson Media Group office.

In addition to her role as owner and media director here at RMG, Anne authors the majority of our blog posts and hosts our BSuite podcast. Favorite topics for both platforms include the entrepreneurial journey, sustainability + social responsibility, media planning, media buying, and forming productive agency partnerships.