A Letter to the Person Who Didn’t See It Coming

A few weeks ago, MarketDesign Consulting celebrated its fifth year in business. Our team gathered in Skaneateles and popped the bubbly as we reflected on the past year and looked ahead to 2024. As a remote team, it’s so important to have the opportunity to be in the same room every now and then, to brainstorm, strategize, and simply enjoy one another’s company.

In this spirit of reflection and gratitude, I have been thinking about how far we’ve come over these last five years and what lessons I have learned since 2018.

Here are five things that I would tell my new business owner self:

1. Not everything will go according to plan. Newsflash. For someone who meticulously planned the first 40 years of their life, this is the most important tidbit I can impart. While I always thought it would be cool to work in an ad agency, little did I anticipate that overnight, I would start a company that would evolve into the 7-figure business it is today. I realized my own resilience and resolve rather quickly, and when faced with a challenge, my instinct is always to look for the solution. Let’s not kid ourselves here; there were plenty of nights spent in the fetal position on the bathroom floor (ala Izzy in Grey’s Anatomy at rock bottom ). Those moments humble you. Especially with the realities of a home, a family, and daycare costs knocking at your door. I started this business out of necessity. I grew this business out of love. What has enabled me to push forward and take the good with the bad, the ups with the downs, is the realization that somewhere out there, someone is seeking the advice I have to offer and needs the services I have to sell.As I reflect on these last five years, I've come to appreciate the power of acknowledging one's achievements. I think so many people struggle, especially at performance review time, to get their accomplishments and achievements on paper. Why is that? Isn't that what we've been working for all yet? Isn't that the exact time (you are literally asked) to promote yourself, your team, and demonstrate your value? I say, give yourself credit for that lesson you learned, that person whose business you helped grow, in real-time and all the time. To me, that’s a far more accurate measure of success than what's captured in an annual performance review. I believe if we could all be better about celebrating our accomplishments and sharing them in a way that’s not boastful, but genuine, authentic, and even a little vulnerable at times, what a different outlook we would have on the world around us and the possibilities in front of us. This one is still hard for me. I am a highly driven and motivated person. So, I keep moving, and I don't take much more than a moment to acknowledge the achievement. When I look back on the months, quarters, and years only some moments stand out; so next year I won't wait until December to reflect on them (I said it here first).
2. Build a culture of accountability, then loyalty. Through my experiences, I have seen the differences between colleagues, leaders, doers, and overachievers; the good and the bad of workplace culture, team dynamics, and personal accountability. There’s nothing worse than being in a situation where you feel like you’ve done everything you can do—being helpful, taking on additional work, supporting other departments—only to reach year-end and realize that, despite your best efforts, you fell short on your own goals. Either you’re handed targets and objectives that you really can’t own or measure; or, in your dedication to being the loyal and supportive team member, you’ve carried everyone else’s stress on your shoulders, with little to show for it.Not everyone gets a trophy, you shouldn't just get a bonus because you showed up to do the job you're paid to do. Meeting the minimum expectations gets you the salary for the job that you have. By setting the right balance of personal accountability and team loyalty, you can begin to empower your team to be their best, with achievable priorities and tangible metrics. Eventually, the words ‘I’ve got you’ don’t actually need to be said. They’re felt and understood.
3. The biggest contracts aren’t always the best. I believe that leadership is not about enhancing your resume but cultivating your character. Until you’ve walked a mile in a salesperson’s shoes, you cannot fully appreciate the weight that they carry. In my early days, I played the role of salesperson, consultant, accountant, executor, visionary, and business owner all at one time. While I never considered myself a salesperson before, as a small business owner, I had to generate new business. I treated every “sales call” I had as a conversation and learned to build a mindset to remind myself "I don't need the money and I'm good at what I do." When I meet with a prospect now, I have a different confidence in this mindset. We are both making a decision to move forward. Now I am setting up the relationship in a different way: a partnership vs. a contract.The proposals you worked hard on, the ones you thought you would win, needed to win but didn’t—those are tough to swallow. I often tell myself now, that if I have to go back and forth on a proposal more than twice, they oftentimes don’t recognize the value we can provide. (…Now, if you ask me in January, there’s something about the new year that makes me feel a lot more generous when the funnel seems less full.) All kidding aside, some of the largest contracts we’ve had have come with the most headaches. And so, no, money can’t buy you love. And money cannot buy you happiness. All things hold true at work and at home. Just because the numbers look good on paper, if you haven’t parted ways with the client who just doesn’t get or appreciate you, it’s time.
4. If you think you’re working too hard, you probably are. If anyone looked at my calendar, you wouldn’t believe that I actually do have a handle on what goes on it, and how it’s used. But for the first time in my professional career, just this year, I started to look at my calendar in two-week increments and push out, or politely decline, what is not urgent or a good use of my time. What this exercise has done is given me actual ownership and accountability over who gets my time and where I’m spending it. I can go to bed and get the eight hours I know I need with a clear conscious. Back in the day, I used to come in on Monday mornings (or sometimes Sunday nights) and blindly accept all. Anything anyone ever wanted me for, I said yes. I needed to be needed. Do you know that feeling? I would feel like every week and every day I was running to keep up. I would constantly get to the end of the week and think to myself, how did I get here and what do I have to show for it? When you freely give your time to others, no matter how much they need it or appreciate it, you diminish the importance of the time you have to do what you need to do and give to the tactics and teams that feed your soul rather than drain it. So now, I schedule my calendar in three ways: (a.) My direct reports get a one-on-one with me every week (we use + teach EOS to run MDCo ), if they want it or I need it. Sometimes it’s to talk about the weather. Sometimes it’s to work through a problem. But oftentimes, it’s to make progress on a series of things that we need to do for a client or a project to move the needle. (b.) I have a mandatory two and a half hours of consecutive time a week that I choose to spend any way I need; and sometimes that’s not at work. Now I know that is okay. Sometimes it's to take a walk or ride the peloton. Sometimes it’s running an errand for my family. Sometimes it’s just to collect my thoughts and figure out how I’m going to do, what I said I was going to do. There is only so much of you to go around; and your family, your team, and your company want the best of you when and wherever they can get it. Clear your mind and then conquer the world. (c.) Lastly, the first thing we do at the beginning of each week is ‘Motivation Monday’. I borrowed this idea from my friend, Frank Piscopo . It’s about learning something new. Seeing things from a different perspective. Trying a different approach. Let me tell you, this has really taken away the ‘Sunday night blues’ by setting the foundation for how we collectively are going to show up, honor ourselves and each other, and grow the business.
5. Do it because you love it. The adage if you love what you do, you won’t work a day in your life is a real thing. One of the MarketDesign core values is "Bring the Joy, " and it was a very intentional choice to have this be a key mantra we live by. For the past five years, on the hardest days and the longest nights, I was at my desk because I wanted to be, not because I had to. Having experienced both really good and really bad work cultures, I know that when you enjoy what you do, who you work with, and what you’re working for—you will make the time to get it done. It won’t be about how much time it takes. It will be about how much joy you get from delivering your best.

?As we take time to pause and soak in the holiday spirit and then quickly watch it fade into grasping the last days of this year, I invite you to reflect on 2023 and perhaps your last five years. What are the words that rattle off your tongue? If they aren’t positive, they don’t excite you, or you can’t pinpoint a time that you are really, truly, proud of, I encourage you to spend these next few weeks writing down on paper the personal and professional goals that are going to make you the person you want to be; by keeping the best of the person that you are.