What I have Learned from My First Three Years in Business

It was 5:30 a.m. and I googled “How to combine two documents in a PDF.”

Talk about living the dream.

There was a lot of googling back in those very early days: How to redact in Adobe, how to add Bates Labels, how to print an envelope in Word, how to do certified mail. This list goes on. We were in lockdown, and just days after launching my firm I had to serve several subpoenas in a case that was set for hearing which had more doctors than lay people on the witness list. I hadn’t printed my own envelopes or done certified mail in over 15 years, and the subpoenas had to go out that day.

Although I certainly wasn’t having “fun” that morning, I now look back on that time with a certain amount of fondness. While the world was engulfed in one massive crisis after another, I was laser-focused on my clients, my new practice, and creating my own vision for what that practice would look like. And eventually the “start-up phase” passed, I am no longer googling at the crack of dawn, and I now have an infrastructure in place which allows me to spend the majority of my time practicing law.

Many people who have their own business describe the first three years as a rollercoaster, but I liken it more to Tilt-a-Whirl. You are constantly spinning and just when you get your feet under you, something comes along, and you have to shoot off in another direction. I leased my first office when downtown Chicago was sparsely populated and the word “Delta” had nothing to do with Covid. “Hybrid” wasn’t a thing yet. Zoom court was supposed to just be temporary. I have a few battle scars that have helped me grow, I see things much more clearly than I did even a year ago, and I am constantly learning each day. Here are my biggest takeaways from the last three years:

Mindset Shift. For my entire 20-year career, I had been an employee. Now I was the owner, and the only one at that. Intellectually, that was not difficult to grasp. But the inherent mindset shift from employee to owner does not happen overnight. This might have been the thing that took me the longest to live into on a daily basis. It wasn’t my job to just service clients. I had to pay bills, maintain a website, take care of signing up new clients, collect fees, and negotiate contracts with vendors. Building those items into my days and weeks to make sure the business kept on track took some time, as well as understanding that these items were just as important as servicing clients.

Know your own strengths and how those translate to your clients. When you are wearing all the hats, unless you want to work 7 days a week for the rest of your career, you have to identify your biggest strengths and make sure you are taking on cases which allow you to work in those strengths. One of my strengths is the rapport I build with clients by listening to them and understanding their goals. As a result, I have built systems to ensure that I have time and space to spend with clients and not just feel like I am on the gerbil wheel each day.

What can you outsource? In the very beginning, I sat through my QuickBooks training and stopped my instructor halfway through the first session. “This is never going to happen,” I said. I had no time to learn the ins and outs of QuickBooks amid taking several depositions. So, I hired a bookkeeper. Where I failed miserably outsourcing was just last summer when I moved my office. If you were walking down Randolph Street in Chicago, you might have seen me schlepping my office belongings from my old office to my new office. Yes, that was me, carting my printer from my office on LaSalle St. to my new office on Clark St. Not exactly the best use of my time.

What can you systematize? I used to think that having systems meant that you were sacrificing a customized approach and funneling all clients into one cookie-cutter formula. Not so. Having solid systems in place allows certain things to go on auto-pilot, such as gathering basic information and client onboarding. The trick is finding the balance between implementing systems that allow you as the lawyer to more quickly get to what you are good at – counseling clients and practicing law. Clients want and need your time. Anything that gives you additional time supplements your client service, not detracts from it.

Scaling your own availability. All lawyers are pulled in a million different directions. Solo practitioners are pulled in ten million different directions. You simply must figure out how to scale your availability so you are able to have face time with those who need it. Time is finite – there are only so many hours in a day. Creating a maximum amount of time to deal with clients, engage in deep work, brainstorm, and work on the business is a huge challenge and there are days where I feel like I am not doing as well as I could be.

Have a short memory but play the long game. It’s impossible to not say “Be a goldfish,” for all of the Ted Lasso fans out there. I made mistakes, and I learned that you just have to move on quickly. As a new business owner, you are making a million decisions. Some will be good decisions, others will be not-so-great. Most will be fine in the beginning, and will need some tweaking to be better later on. I tended to buy more technology than I actually needed. I had multiple platforms that were doing the same thing and was overpaying on subscriptions. I cancelled several when they came up for renewal and moved on. You make so many decisions you can’t get hung up on the ones that don’t pan out exactly as you hoped. If you hope to be in business for a while, you learn from your mistakes, and it gets easier.

Trust your gut and do you. Some of the best advice I received was from a good friend who had run her own firm for years. When I was contemplating renting my first office, she told me to stop listening to what other people, no matter how well-intentioned, were projecting on to me when giving me advice on how to spend money. Only I knew what my own books looked like and when it would be right for me to take on more expenses. My approach was somewhat conservative in that I gradually took on additional expenses as I needed to. Others might have been more aggressive and others, even more conservative. The lesson is to just do you. Only you know what is best for your business.

You cannot be in overdrive all the time. There is power in a pause. A year and a half into the business, I completely paused and just focused on the practice of law. I was in overdrive, exhausted, and felt I needed to get a better handle of what I had put in place rather than keep doing more. I’m not going to lie, that was hard. I’m a doer. I’m happiest when I am checking off tasks and moving towards a goal. But the power in such a pause came from observation – seeing how certain systems I had put in place were working and getting a better understanding of what I needed. Out of that period of just being still came a period of tremendous prosperity because I had clarity.

The good days are great, and the bad days will not last forever. Boy that’s the truth! The highs are much higher as an entrepreneur and the lows are much lower. When I was opening, I had the most horrendous experience with my bank (which I am refraining myself from naming here) and getting all my proper accounts opened. I had to go back to the local branch four time, yes, four times, to get everything squared away. Accounts just were flat out not opened. Paperwork was lost. The branch closed for over a week because a worker got Covid. Nothing was getting processed, and no one from the bank bothered to call and tell me that. I even showed up with an appointment and no one was there to meet me. I thought I was losing my mind. Eventually everything worked itself out.

Find your tribe. This might be the most important piece of advice. If you are going to open a business, any business, and be a solopreneur – you must find your support system. I have multiple support systems in place, and they have been critical to my success. You need to have colleagues in your field on whom you can call with questions, to brainstorm, and to commiserate with (so important!). You also need to have a brain trust who can step back, see your challenges and opportunities, and provide you with unemotional advice. And you need your cheerleaders – those people who are in your corner rooting for you and there to pick you up when you need it. Going solo does not mean that you have to feel alone. There are people in your same boat who are looking for connection. Reach out to them. You will be surprised how many people are willing to help.

A strong business is in constant motion. The first few months I was open I felt like I was drinking from a water hose. It just never stopped. And I would tell myself, “As soon as I get this done, I can settle in.” And there would be something else. And then the next thing would come around that I either wanted to do or needed to do. And then the next. After about 18 months I realized – this is what it means to run a business. You are never done. The business is constantly evolving, as is the industry. You don’t need to be making changes every week. (I did that at one point and that was when I overbought on my technology.) But you should flex that learning muscle consistently.

AI. What is there to say? Well, a lot probably. But I am keeping with my pledge that I will not contribute to the noise when I do not have something meaningful to say. I simply do not know where AI is going yet in the legal world. But it’s here and we are going to have to deal with it. Potential clients are constantly seeking alternative legal service providers in order to cut costs and avoid hiring lawyers. It is likely AI is going to impact that segment of the market. We are not the only profession which will need to increase our quality of human service to compete in an ever-changing marketplace by offering services AI cannot: empathetic and thoughtful counsel, creative legal ideas, and collaboration with technology to streamline the client’s experience. I will go out on a limb and predict that the lawyers who can be forward-thinking and harness AI to support their practices so that they can continue to maximize what they do best will come out ahead.

The legal industry will most likely look extremely different even just five years from now. It remains to be seen what the hybrid work environments will look like this time next year. AI and technology are coming at us from all directions, and yet we, as lawyers, must remain steadfast in our responsibilities to our clients and to our profession. I’ll check in with you after year five! It will be interesting to see how this article ages.