Can it be twenty years? Really? In 1999, I hatched a plan and stepped out into the unknown of business ownership.

But how did I land here? Sure, I flirted with the idea of being a freelancer designer/marketer in my 20’s. But building a client base and filling in much of the needed business acumen was not quite my forte yet. So I got the next job while I plotted to open a nightclub instead. (Yes, nightclub. That’s what the line in my bio about DJing is about.) This time, I went to workshops held by the Small Business Administration and learned how to write a business plan.

My caveat: We had to be fully financed for the start-up and first year operations before signing a lease and diving in. After a year — and 30% shy of the budget goal — I stayed true to my goal. That plan was sacked and I moved to Chicago to find more opportunities. (And by opportunities, I meant for better jobs and better access to music and art!)

Hello Chicago and Birth of the Web

After a few weeks temping, I landed a desktop publishing job with the Medical Library Association. Great staff supporting thousands of dedicated librarians in health sciences universities and institutions around the globe. It was a good fit and I found myself promoted to manager, then director of the department in a couple of years.

But a vital development during my stint at MLA was the advent of that game-changer of all changers of games: the World Wide Web. When our librarians first requested a website to promote their upcoming conference, I stayed late night after night to learn basic HTML coding and styling for this amazing new tool. It brought together everything I loved to do! Design. Write. Promote with visuals and video (well, some of that took a bit for the bandwidth to catch up). It was fantastic. I quickly expanded the department beyond publications with a side of marketing to be a full communications team with website support.

A few more years and a couple of iterations of the association website and I was ready to make a shift. I landed a gig with a statistical software company marketing their science division. Turns out, I’m not the best fit for a large corporate outfit — especially one that wasn’t eager to value their customers. In a matter of months I decided to enroll in graduate school, give notice and launch what would be Grotto Communications.

Entrepreneur Much? Hitch a Ride with the Hive

I clearly remember my first day at Grotto Communications come January 1999. I marched into the spare room with the big metal desk (scavenged from MLA during a remodel) and started with the brass tacks of setting up a filing system, designing a logo and mapping out how to lure clients. My last two employers were among my first clients and I hit the ground skipping.

The graduate program in DePaul University’s School for New Learning was perfect support as I crafted much of my own curriculum structured around growing a freshly-hatched marketing business. The coursework covered basic principles such as teamwork, ethics, etc., and my cohort of students was from many different disciplines including law, psychotherapy, technology. Discussions and presentations were fascinating as we all brought real-world experience to share and dissect.

That collective concept was exactly how I wanted Grotto to work. (In fact, I had the vision for it before I even knew about the graduate program.) I wasn’t interested in opening up an agency, hiring a bunch of people and generating work to keep them busy. I wanted to help business and not-for-profit runners get access to more sophisticated marketing and communications approaches by bringing in colleagues who were the right fit and only as needed.

The internet, email, then cell phone tech started to make this easier as the years went by. But as the millennium turned, I would get puzzled looks from prospective clients as I explained how we put together teams based on what the project actually required. A friend and colleague understood what we could provide and hired us to promote and expand an independent physicians group. Over four years, our fluctuating team sometimes numbered a dozen in providing marketing, design, public relations and event services. Grotto was now incorporated and felt firmly established. A move to Evanston from Chicago provided more room in my home office, but didn’t affect the workflow a bit.

Our Social Networks: Face-to-Face & Screen-to-Screen

The expansive physicians group project ended rather swiftly as their internal politics played out. It wouldn’t be the only big wave of change at Grotto. The next step would involve expanding the sphere of influence to join local chambers of commerce and get to know the business community. I admit, I expected these groups to be rather stodgy and wasn’t sure how it would fly with my hive. But the support and friendship found in these Chambers was terrific. Once again, I found connection with different kinds of people and a place where small businesses were really appreciated. Trust ensued and the work grew out of those relationships.

I’ve now been a member at various times in four or five area organizations, including serving on the board for Lincolnwood and on the Marketing Council for the Evanston Chamber of Commerce. The Evanston Chamber always felt most like home (well, the town was actually home) and even as it has changed over the years, the camaraderie between members is a real treasure. Lots of opportunities to learn or lead or just grab a glass of wine and commiserate about a challenging day.

This engagement with actual communities ran parallel for me with the dawn of social media as advertising and customer communications began some of the biggest transformations in marketing yet. I hopped onto Facebook and the others to start learning much and helping my clients navigate beyond traditional avenues like print and radio advertising. Ever the advocate for “integrated” marketing communications, finding ways to expand helpful content throughout websites and social media outlets continues to be challenging and fun as hell.

So Where Do We Go From Here?

Like anyone else, my life ebbed, flowed and changed in waves big and small across all twenty of these Grotto years. I’m not even going to elaborate on the change in partnership status (a.k.a. divorce) due to time and vexation. But through all those slings and arrows, Grotto and I seem to remain flexible and resilient.

I’ve learned along the way that walking away from something (clubs not to be, jobs that don’t fit, partnerships that have run their course) often leads you to the best next things. Embracing the new ways of being and doing business can get frustrating. Are we supposed to learn how to integrate Snapchat or is that already over? How can we switch up email tactics to help people get useful info without royally ticking them off? And how on earth do we keep track of all these moving parts?

The good news is that the emerging options can still prove to be exciting and fruitful when promoting organizations of all sizes and flavors. Today, we’re exploring how voice search works differently from typed search queries. Geo-location apps and review sites (now there’s a hive!) are creating new pathways to connect people with the products and services they want and need. And the basics of crafting clear words and images to communicate effectively can still be applied in this latest frontier.

When I moved to Chicago and started riding the “L” to work I quickly learned that, if you have to stand, you’ve got to keep your knees flexed in order to stay upright. I likened it to riding a surfboard (despite the lack of waves in my native Kansas, mind you). Stay flexible and the speedy, sometimes choppy rhythms of the train are less likely to toss you into another commuter.

And that’s just want we need to do to handle times of transition, uncertainty and growth on all fronts. I’m sure I’ve changed nearly as much as my business has over the past two decades. But reflecting on this journey has made me grateful for learning how to embrace change and to help my clients thrive by doing the same.

Thanks to everyone who has supported me and Grotto throughout these years! Our web of connection is strong and flexible. I’m truly grateful for each and every client, colleague, vendor, playmate, guru and pal along the way. Cheers to the next wave!