A Conspiracy of One

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Michael Grossman. Photos by Callie Lipkin

There’s a bottle of champagne in Michael Grossman’s refrigerator. Or so his wife says. Grossman hasn’t actually seen the bottle, and he doesn’t want to. Better to wait, he says, until he lands a new client, until a settlement check comes in—until something happens that he feels is actually worth celebrating.

But that might just be the fear talking because today, Monday, Sept. 17, 2007, is Grossman’s first day at a new firm. His firm.

The Law Office of Michael R. Grossman sits at the end of a long corridor on the second floor of a vintage building in Evan­ston, a suburb of Chicago. Actually, it’s more like a cubicle in a shared office space. But it’s a cheery space—an expansive loft where light streams in through skylights, loops of wires wind around rafters and the tall, gray partitions never look too corporate against the brightly painted walls.

Grossman is the only attorney among the room’s group of professionals, which includes a financial adviser, a computer programmer and a public relations representative—a situation Grossman views as ideal for its client-building possibilities. He plans to focus his practice on estate planning, a practice area he’s interested in and one that he feels is manageable for a solo practitioner. That said, he’s already talked with the computer programmer about possibly reviewing a terms-of-service agreement for him.

So far, that’s his only line on legal work. And he’s definitely feeling the fear. After putting some books away in his bookcase and situating his vase of sunflowers—a send-off gift from his family—he’s ready to tackle the day. Which for now means stuffing hundreds of envelopes with announcements that he’s opened a solo practice. Grossman is sending the cards to pretty much everyone he knows: friends, associates and lawyers he’s crossed paths with during his nine years in the Cook County Public Defender’s Office.


It’s not high-level legal work, but it’s important nonetheless, if for no other reason than to keep him busy. Grossman’s used to being busy. Until the Friday before his solo start date, he specialized in forensic evidence such as fingerprints, ballistics and DNA. His primary responsibility was to assist PDs working on cases involving forensics.

It was challenging work, and Grossman enjoyed it. He liked everyone in his office, the benefits were great, and his hours were a fairly consistent 9 to 5 with plenty of flexibility available as long as he was able to get his work done.

“In many ways, it was a dream job,” he concedes—especially when his wife, Nina, gave birth to twin boys 2½ years ago. But he couldn’t shake the feeling that there might be something else out there for him, something else he could or should be doing.

Around that time, his wife’s maternity leave was ending. They didn’t feel comfortable putting the 4-month-old infants into day care, so Grossman decided the time was right to take a break and stay at home for a while. He cashed in his vacation time and took advantage of an office benefit that allowed him to take an unpaid leave of one month for every year he’d worked. Over the next 10 months, his plan was to care for his sons, think about his career and “await an epiphany.”

The epiphany never came. Between the diapers and the housework, he was exhausted. Yet he did arrive at an important conclusion: “I missed being a lawyer, I missed going to an office and I was ready to go back.”

Back to what, though, he still didn’t know. Grossman responded to a few ads from civil litigation firms looking for associates. But he soon realized that, as essentially a new associate, he’d have to work new associate hours, minus the flexibility that he wanted to have as a new father. Case oversight was another sticking point. At the PD’s office, cases “were mine to do with as I chose, and I had that trust.” He wasn’t sure he was ready for someone telling him what to do all the time.

When he returned to work in May 2006, he did so enthusiastically, with batteries recharged and a renewed sense of conviction. It didn’t last. He began to notice the violence was getting under his skin in ways it never had before. Before he became a parent, that is. “The pleasure that I had going back to work was tempered by the cases,” he explains. The cases “were rummaging around in my brain, the ME photos, the fact patterns.”

One murder case proved particularly troubling. “There were four dead bodies, and one was a 2-year-old,” he recalls. “I had medical examiner photos in my file that I didn’t want to look at. I didn’t want to take that home with me at the end of the day.” While the case alone wasn’t enough to make him quit, it contrib­uted to his growing malaise. “I believed in what I was doing,” he says. “I just wanted to do something different.”

Meanwhile, Grossman had become an avid blog reader. He’d started with legal technology topics, which he’d peruse during the children’s nap times and in the evenings, when his wife, a high school theater teacher, graded papers. These blogs led him to others, many written by solo practitioners. He became a regular reader of Susan Cartier Liebel’s Build a Solo Practice blog and joined some Illinois State Bar Association section e-mail discussion lists. He also joined Solosez, the ABA’s General Practice, Solo and Small Firm Division e-mail discussion group. (Although he’s an ABA member, membership is not required to participate).

Solo practice was something Grossman had never before considered, but reading about what these solos were doing—working out of their homes, leveraging technology to maximize flexibility—held definite appeal. He began to believe it was something he could do, too.

He floated the idea to his wife, and she was instantly supportive. “She knew I had wanted to do something different for a long time. I had bad days and the subject matter was getting to me, and she was seeing it more often,” he says. “She thought the idea was great—as long as I put the pieces into place. She said, ‘Go work on that.’ ”

He spent the next six months planning his practice and strategizing everything from which printer to buy to when to tender his resignation. He hit the estate planning books and boned up on law office technology via blogs like the Mac Lawyer and an e-mail discussion list called Macs in Law Offices. He even started his own blog, Practical Lawyering, to chronicle his path to solo practice, albeit anonymously.

Perhaps most important, Grossman stepped up his involvement on the solo e-mail discussion lists.

“Without them,” he says, “I don’t know if this would have been possible. If you’re going solo and you don’t know anyone else who has done it and you don’t have any sort of collective wisdom, it’s damn near impossible.”

It’s all part of building something from nothing, of starting from scratch without even a base of prior cli­ents to approach for new business. “All my former clients are indigent—if they’re not in jail,” Grossman deadpans. “At the top of their list is not making an estate plan or needing help in a domain name dispute. They’re probably going to be thinking about how to make rent or get food on the table.”

Hence the giant box of announcements sitting on his desk. He’s got sheets of address labels printed out and rolls of stamps at the ready, but he admits the process isn’t moving as fast as it could. He’s still recovering from the weekend, which he spent at a Wisconsin cabin with a group of buddies. So it’s off to the kitchen for another cup of coffee.

Grossman found his office space via Craigslist. It was only the second listing he looked at, and he was instantly sold. After all, the rent was low and it included the desk and high-speed Internet access. There was a private conference room complete with French doors, and the location was convenient to the ultimate business trifecta: a bank, a Starbucks and an el stop.

Grossman had originally envisioned setting up shop in his basement but quickly realized that wasn’t going to be productive. “Plus my kids are noisy,” he adds.

Having an actual office also gives Grossman a professional-looking place to meet with the clients he hopes will come to him with their estate planning matters.

His initial goal is to attract clients not unlike him and his wife—“people whose estates certainly aren’t complex, but who have kids and need to make sure they’re taken care of.” They’re people who have some money for legal work but want to know they’re paying for services, not fancy office space.

The easiest path would have been to practice criminal law, but Grossman wanted to make a clean break (although at this point, he concedes that he’d take a DUI or a small criminal matter, provided the client was a paying one).

He’d also like to get into intellectual property—he has an LL.M. in information technology, which includes the study of laws involving the Internet, computers, copyrights and trademarks. Some general business formations would be good too. Maybe a few real estate closings. What he knows he doesn’t want to do is adoption, employment law and family law.

Part of the appeal of estate planning is that it allows him to mix hourly rates and flat fees, depending on the complexity of the work. Whatever he charges, he plans to have it all spelled out for his clients.

From talking with other solos and what he’s read on the topic, he understands the importance of a well-written fee agreement—and drafting one, along with engagement letters and nonengagement letters, tops his to-do list this week. He plans to create his own versions based on samples he’s received from other solos along with advice set out in his well-read, heavily highlighted copy of Jay G. Foonberg’s How to Start & Build a Law Practice.


It’s important to Grossman to have everything ready to go the minute the business starts coming in. “People are going to come to me with legal issues that I don’t know the answer to, and I know that. There’s no way to prepare completely for the legal issues that will come, but my goal is to prepare in an administrative and organizational way so that I’ll be prepared to do the legal work and I won’t have to worry about the other stuff,” he says.

Being prepared will also underscore the type of professional image he wants to project to his clients. “I am an attorney in a small town, but I don’t want to be seen as small or small town,” he says. “I am a competent attorney starting out, and I offer good value and comprehensive, effective representation.”

Grossman knows that his ability to remain a solo practitioner rides on careful financial management. Setting up his practice, he’s been extremely mindful of where to spend and where to save.

His desk chair, bookcase, file cabinet and computer came from home, and Grossman did extensive research before dipping into his savings for the filing fee to set himself up as an LLC and for the $2,500 or so he spent on software and hardware such as a networked laptop for home, a printer and a scanner. He also set up some nifty—and free—online office-tech services like GrandCentral, which forwards office calls anywhere he wants them to go, plus takes phone messages that can be accessed via e-mail.

Where Grossman splurged was on creating a professional, unified image. He spent about $600 to hire a graphic designer to create a stylish logo, a Web site and full-color business cards. “I didn’t want to look like a solo on a shoestring,” he explains.

When it comes to actually running the numbers involved with staying in business, however, Grossman has only a general idea of what his ongoing expenses will be. What he does know is that his family has made do with less, and they were OK.

Now, of course, he’s got the added expenses of office rent and day care. “I’d consider myself a great success if I can make as much as when I left the PD’s office,” he says. That means around $70,000 a year, give or take a few weeks of vacation, plus the ability to “accept the clients and subject matter I want and theoretically having more control over my time.” Also on his wish list: a virtual paralegal service, a few more file cabinets, a cop­ier and the freedom to do some pro bono work.

Grossman has given a tiny bit of thought to what it might mean if he is wildly successful. “We’d add another dormer to the second floor, maybe expand a bathroom,” he muses. Mostly, though, he’s realistic. “I realize the top income for a solo practitioner is around $80,000—maybe $100,000 or $120,000 if you have a real niche—so I have no fantasies about a Bentley. I’d just be content to make what I used to make.”

The thought of failure has also crossed his mind. “I am optimistic, but I have told myself that if I am not making money by a certain point in time, I’ll go and do something else,” he says. “I don’t have a date in mind, but I also know I’m not going to sit around here waiting for the phone to ring.”

When it rings—and Grossman hopes to hell it does ring—it will mean a motivation and intensity level far above what he was used to at the PD’s office. “I feel bad saying that because the clients I worked for before had their liberty at stake, and perhaps that’s the most precious thing after your kids, but I wasn’t my own boss,” he says.

Now he is. He’s got something on his schedule nearly every day this first week in business, including a Chi­cago Bar Association committee meeting and an Evan­ston Chamber of Commerce social event. His goal is to network with other lawyers; since he can’t rely on his former clients to bring him cases, he’s hoping the lawyers he meets might result in some referrals.

Grossman’s last paycheck from the PD’s office will arrive in two weeks, and then there will be nothing—except the anxiety. “I can have the best space, the best computers and the best intentions, but until and unless someone hires me, it’s not going to matter,” he allows. “Then and only then will I believe in a real and concrete way that this is doable.”

Web Extras

The Law Office of Michael R. Grossman: An Update

Michael Grossman’s blog, Practical Lawyering

David Freeman’s Five Elements of a Successful Client-Development System

Michael Grossman’s Favorite Web sites


Saving Money: Demand and Supplies

Running a successful solo operation is all about economics. Here are three ways Michael Grossman saved money starting out:

Minimize furniture expenses. Grossman’s leased office space came with a desk and a furnished conference room, and he brought his furniture—a desk chair, a file cabinet and a bookcase—from home.

Maximize bar association benefits. Grossman reviewed the member benefits offered by the Illinois State Bar Association, the Chicago Bar Association and other groups to find the best package of perks for his business. Through his memberships, he snagged free legal research resources, a sweet deal on malpractice insurance, and opportunities to attend section meetings and seminars that are right on point.

Go postal. Instead of contracting for a postal meter or signing up for online postage, Grossman simply orders stamps for their face value from the post office’s Web site, which delivers them along with his daily mail.

Tips from Other Solos…

We asked some established solos to share their best advice for Michael Grossman and others just starting out. Here’s what they said:

“Always err on the side of flexibility. Be willing to pay for contracts such as leases and computer research, which are shorter and slightly more expensive. This way you can reassess your needs at the earliest point available to you. It is hard to predict what will be important to your practice after you go through your first year, so you do not want to lock your costs in too early on.”

Liz Goldstein, Camp Hill, Pa.

“Assuming that you are having to find health insurance— perhaps for a whole family, for the first time—allow many more weeks or months than seems necessary, and use a good personal insurance broker who deals with multiple insurers.”

Shell Bleiweiss, Chicago and Barrington, Ill.

“My advice to attorneys who are thinking about going out on their own is to first create a thorough budget plan before starting up shop. … Bottom line, if the first year looks to be out of your budget, then it’s best to stick with your day job a little while longer.”

Nick Dang, Bellaire, Texas

“People are complicated, law is simple; complicated people and their problems can be solved with methodical analysis of the law.”

Dick Howland, Amherst, Mass.

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