Part Two: What Four Years Has Taught Me about Building A Business

Welcome back! If you caught Part One of this series you already know how much the clients of Chalk Consulting have shaped these past four years. Today I want to get a little more personal. I want to talk about what it actually feels like to build a business from scratch, the lessons that humbled me, the ones that surprised me, and why I enjoy sharing the lessons learned other people who are just starting their own journey.

Because running your own business is a wild, beautiful, sometimes terrifying ride. And I would not trade it for anything.

You Know More Than You Think You Do

I was talking with a friend the other day who has been running their business for nearly a year. The questions they were asking got me thinking and I said, “oh goodness, I know what’s going on, because I felt this my first year, you are in the imposter syndrome phase.” In the early days I would catch myself questioning myself and the value I bring to the clients. And the answer, which I now know with complete certainty, was yes. I did know. But it took time and experience and a lot of just doing the work to fully believe it.

Imposter syndrome is real and you have to push through it. You have to keep showing up, trust your instincts and let your results speak louder than your doubts. If you are out there right now second guessing yourself, please listen, you know more than you are giving yourself credit.

Build Your Posse and Protect It

Nobody does this alone. One of the best decisions I ever made was intentionally surrounding myself with other consultants I could actually lean on. Jenny Carrillo and Laura Alexander of Alexander | Carrillo Consulting, Mike Bassoff of WB Charter Development, Clint McCall of Brighton Advisors, Alice Ferris of Goal Busters, Jason Shults of JNS Data Consulting, Leslie Crist who helped with some grant writing, and Jeannine Mason of J9 Brandworks. These people are in my “consulting posse” and I count myself incredibly lucky to have them in my corner.

Often the business world does not celebrate healthy competition. Jenny, Laura, and the entire Alexander | Carrillo team are consultants in the same lane as me. They have been nothing but supportive, encouraging and genuinely kind. That says a lot about who they are. What I have learned is there is plenty of work and the right people know that. Don’t mistakenly think you have to claw your way to being the top of anything. I am grateful to find people who support each other by lifting them up and being happy about their success.

The Chalk Consulting Advisory Council

Something intentional that I built along the way is the Chalk Consulting Advisory Council. These are trusted individuals I hand selected to be a sounding board, a source of wisdom and a steady presence when I need guidance. They are not my day-to-day collaborators; they are a different group. They are the people I can pick up the phone and call when I am navigating a big decision, thinking through a new direction or just need someone in my corner who understands the work.

Building an advisory council is something I would encourage every small business owner to consider. You do not need a big formal structure. You just need a handful of people who believe in what you are doing, bring diverse perspectives and are willing to show up for you when it counts. That kind of support is priceless and helps keep your business and mindset on track during the speedbumps or transitions.

Learning from Leadership

Four years of client work will teach you a lot about your craft. But if you pay attention, it will also teach you a lot about leadership. And I have been paying close attention because the leaders I work with help me continue to grow and shape who I am. The CEOs, Executive Directors, Presidents, Athletic Executives, Lead Fundraisers and the members of the Board of Directors I have had the privilege of sitting across the table from have each brought their own style, their own vision, and their own way of moving through their careers. I have taken something from each of them. Watching how they lead, how they make decisions, how they rally their teams and how they manage the difficult moments has been a valuable form of professional development.

Get Your Vendors Right From the Start

From my experience in higher education, I knew vendors were important. The vendors and support systems you put in place are another “posse” and the backbone of your business. It helps to have the right people around you make everything run smoother. Let me just share who has made a real difference for Chalk Consulting because maybe it helps you too.

For branded items, Holly Polston of Garment Graphics has been fantastic. My website would not exist without the talented Claudia Tinnirello at Sophisticated Cloud Limited. Payroll is overseen by Joey Medina at Journey Payroll. My accountant John O’Dowd who handles taxes and Kelly Medvec who helps me with bookkeeping. And when I need legal guidance I am so grateful for attorney Johnny Helenbolt. Don’t overlook your insurance needs either. They evolve as your business grows. For me, I had to look at special event to cyber insurance needs and Phillip Drachman at Drachman Insurance has been a tremendous resource.

For day-to-day communication strategies and keeping everything running, a huge shoutout to Victoria Hanley who has helped me with graphics design work and communication efforts and to Brenda Filippelli who was such a steady support when I was first getting started.

Oh, and one more thing, you need to get a city business license. I found that out after year one when I got a notice about not having it.

Your posse and vendor support system is about more than your bandwidth. It is about using your social capital wisely and knowing that when you bring the right people together at the right time, you can do so much more than you ever could alone. Find your people and share gratitude often.

Find Your Space and Own It

Something that sounds small but made a huge difference for me was finding a place to work that was outside my home office. Sometimes the timing of things at home doesn’t work well and going back and forth won’t cut it. I needed a space where I could show up, get focused and feel like a professional. The Arizona Sands Club co-working space changed the game for me. Having that dedicated environment opened up new opportunities, new connections and honestly just gave me the energy and focus I needed to do my best work. If you are working from home right now and feeling scattered, look into co-working spaces in your area. It is worth it.

Interns: One of the Secrets in Business & Mentorship

Okay, I have to talk about interns because this is something I am genuinely passionate about and I do not think enough small business owners take advantage of it. I have previously shared this concept in Chalk Talk with Phoebe blogs and on LinkedIn. When I was at the University of Arizona I used interns constantly and in every position I had on campus. I built robust internship programs because I saw firsthand the value they bring, not just to the organization but to the students themselves. Someone took a chance with me when I was a freshman and I pay it forward.

Bringing interns into Chalk Consulting has been one of the highlights of these four years. They keep you grounded, push you to stay current with new technology, and help you see the world through a fresh lens. Often, they teach you just as much as you teach them. There is something so energizing about mentoring a young person who is hungry to learn and watching them grow. I enjoy it.

With that said, getting interns is more accessible than you might think. Many universities offer internship programs as part of their coursework, which means students are actively looking for real world experience and sometimes it is at little or no cost to you as a business. Keep in mind that the Fair Labor Standards Act does not allow a for profit-business to have college students volunteer. For profit-businesses must pay these individuals unless it’s part of an official course credit internship. To find these students you just need to do a little research and reach out. If you happen to be in Tucson, I have some great leads for connecting with interns through the University of Arizona. Feel free to reach out and I will point you in the right direction!

Trust the Process Even When It Gets Messy

Here is something nobody tells you when you go out on your own. Not every client follows through the way you hoped. Not every idea lands the way you pictured it. And sometimes things just do not go the way you planned. It makes sense and that is okay. You keep grinding. You keep pushing. You keep believing in what you offer.

You pick up the phone and call another consultant. You ask a friend to look something over. You brainstorm with people you trust. When you leave a big organization you miss those water cooler moments more than you ever imagined. So, you build your own version of that, and you protect it fiercely.

The Learning Truly Never Stops

Four years in and I am still evolving. New clients bring new challenges. New collaborators bring fresh perspectives. The nonprofit and fundraising world keeps evolving and staying sharp means staying curious. I love this work. For the sports person in me, there is no finish line and that is exactly how I like it.

As Chalk Consulting steps into year five I am more energized and fired up than ever before. There are clients I have not met yet. Communities I have not had the chance to serve yet. Ideas that have not even formed yet. And I honestly cannot wait.

Thank you for being part of this journey. Whether you have been a client, a collaborator, a cheerleader or just someone who has read these posts, it has meant more to me than you know. This work is better because of the people in it, and I am better for the friendship and collaboration.