By Jerome Dees, Host of Cater Caffeine
If I could start my catering career over today, with everything I know now, I wouldn’t change the destination. I would change how I got there.
My career has been full of great wins, meaningful relationships, and opportunities I’m deeply grateful for. But it’s also been shaped by missteps, blind spots, and lessons I learned later than I should have. Those lessons are what I want to share, because most of them have nothing to do with tactics and everything to do with how you show up.
You Are Building Two Brands at the Same Time
Early in my career, I thought I was only building the brand on my business card. What I didn’t fully understand is that I was also building my personal brand and reputation with every interaction.
Customers don’t just remember the food. They remember how you made them feel. They remember whether you listened, whether you were honest, and whether you showed up when things got complicated.
Looking back, some of the customers who mattered most followed me from job to job. That didn’t happen because of menus or pricing. It happened because of trust. If I could start over, I would be far more intentional about treating every interaction as a long-term investment, not a short-term sale.
Sometimes Saying No Is the Right Move
One of the most counterintuitive lessons I learned is that saying no can actually strengthen relationships.
Early on, I tried to bend too much. I wanted to accommodate every request, even when I knew it pushed the limits of what our brand or team could realistically deliver. That often led to mistakes, refunds, stress, and apologies.
Over time, I learned that honesty builds credibility. If something isn’t a good fit, it’s better to say so. Referring someone to another provider, or steering them toward a simpler option, often earns more trust than forcing a sale. Many of those customers came back later for events that were a better match, because they knew I wasn’t just trying to sell them something.
Focus on We, Not Me
There was a stretch early in my career where I was overly focused on myself. My visibility. My recognition. What I wasn’t getting.
That mindset never served me well.
Everything changed when I shifted my focus to “we.” When I invested more energy into supporting my team, developing others, and helping people succeed without expecting anything in return, my own career accelerated.
Helping someone else get promoted led to opportunities I never could have planned. Strong teams create strong leaders. If I could go back, I would spend far less time worrying about how things reflected on me and far more time asking how I could make the people around me better.
Own Your Calendar Before It Owns You
Sales professionals are ultimately judged on results. No matter how busy you are, no matter how many meetings you attend, reviews almost always come back to numbers.
If I could start over, I would aggressively protect my calendar. That means blocking time for selling, follow-ups, and relationship building, and clearly communicating the value of that time to leadership.
When you can articulate the opportunity cost of losing selling time, conversations change. Owning your calendar is not about being unavailable. It’s about being intentional.
I would also schedule personal development the same way. Reading, learning, networking, and reflection are not extras. They compound over time. Waiting five or six years to prioritize growth was one of my biggest mistakes.
Treat Internal Customers Like Real Customers
I’ve always done fairly well building relationships with teams on the ground. Where I fell short earlier in my career was with internal stakeholders above me.
Looking back, I was sometimes combative when I thought I was right. I pushed too hard. I focused on winning arguments instead of building alignment.
What I understand now is that internal relationships matter just as much as external ones. The people you work with today may be the people who open doors for you tomorrow. Even when you disagree, professionalism, empathy, and patience go a long way.
If I could start over, I would focus on being the least of someone’s concerns. Reliable. Prepared. Respectful. Those traits build trust faster than being the loudest voice in the room.
Start Networking Sooner Than You Think You Should
Networking isn’t just attending events and handing out business cards. It’s building real relationships over time.
Some of the biggest opportunities in my career came from small, seemingly insignificant interactions. Sitting on a panel. Grabbing coffee. Helping someone without expecting a return. Those moments compounded.
I wish I had been more intentional about networking earlier. Internally. Externally. Across roles and organizations. Visibility matters, but authenticity matters more. People remember how you show up.
Protect Your Energy and Your Health
There was a period in my career where I equated exhaustion with commitment. Long hours. Skipped lunches. Constant pressure.
No one remembers that you worked seven days a week. They remember whether you were effective, consistent, and steady.
Burnout makes you less disciplined, less patient, and less sharp. If I could go back, I would take better care of myself. Breaks are not a weakness. They are a requirement for sustained performance.
Choose Your Boss Carefully When You Can
You don’t always get to choose your boss, but when you do, it matters more than you think.
If I were starting over, I would ask better questions during interviews. About turnover. About stress. About how success is measured. About how obstacles get removed.
Your manager shapes your experience, your confidence, and often your trajectory. Being thoughtful here can save years of frustration.
Use a Scorecard Earlier Than You Think You Need One
This might be the biggest technical lesson I learned too late.
A simple scorecard changes everything. It turns effort into visibility. It answers questions before they’re asked. It removes emotion from performance conversations.
If I could start over, I would build scorecards early. Weekly plans. Weekly recaps. Clear metrics. Visual progress.
Every year I had a written plan and shared it, we hit our targets. Alignment creates momentum.
Small Choices Add Up
None of these lessons are dramatic on their own. That’s the point.
Careers are shaped by small, consistent choices. How you treat people. How you manage your time. How honest you are. How prepared you show up.
If you’re early in your career, you don’t need to have everything figured out. You just need to be intentional. You can start today. You can decide to show up differently. Those changes will be noticed.
And over time, they will change everything.
About the Author
Jerome Dees is a catering sales leader, speaker, and the host of Cater Caffeine on CaterLinked. With nearly two decades of experience in restaurant and catering sales, Jerome has led teams at scale and worked across multiple service models, from corporate drop-off to full-service catering and private dining. He is known for his practical, people-first approach to sales, his focus on internal customers, and his ability to translate performance data into clear, actionable insights. Jerome is passionate about helping catering professionals build confidence, credibility, and long-term career growth through preparation, consistency, and strong fundamentals.
