Going Solo

Six attorneys on the joys and challenges of hanging a shingle

Published in 2021 Oregon Super Lawyers magazine

By Steve Knopper on July 12, 2021


If you’re an attorney working alone, you’re not alone. Last year, 26% of respondents to an American Bar Association survey were solo practitioners. 

There are as many reasons for hanging a shingle as there are for becoming a lawyer in the first place, including the desire for opportunity and independence. And though hanging a shingle means playing with your own stakes rather than the house’s, all six Oregon soloists we spoke with came out ahead. “Now,” says criminal defense lawyer J. Robert Moon, “I don’t worry at all about money.”


Laura A. Fine, Law Office of Laura A. Fine; Criminal Defense; Eugene: For my first five years, I was a legal aid attorney at Lane County Legal Aid. I left to try to make a bit more money, and got a job at public defenders. I loved my work, but I was working nights, I was working weekends, and I started to recognize there could be negative health consequences trying to keep up with this broken system. After six years I said, “I can’t do this.” A couple weeks after that, somebody offered me a job representing law-enforcement and public-safety labor unions. I found it easy, and not very stimulating, so I applied for a job with a business attorney. He took me to lunch and told me to open my own practice. He said, “You can do it. Keep your overhead low, treat your clients like gold and you will be OK.” I am eternally grateful to that attorney.

Jeff Wong, Attorney at Law; Tax; Portland: I started with the IRS chief counsel office in Laguna Niguel, California, in December 1984. It was very clean work. But the office I was stationed in was slated by Congress for 16 lawyers, and they ran out of money and we ended up going with five. We were five people running one of the largest IRS districts in the country. The caseloads were enormous. I ended up being assigned my first million-dollar tax case within the first year, my first $10 million tax case within the first two years, and a Chapter 11 bankruptcy case for a Fortune 500 corporation at two and a half years.

J. Robert Moon Jr., Attorney at Law; Criminal Defense; Baker City: When I came to eastern Oregon, there weren’t that many criminal defense lawyers, and I was able to do big cases early. I was on the defense team that won the state’s first aggravated murder case—and I’d only been a lawyer for seven years. I tried another murder case when I was with the firm. I tried lots of sex abuse cases.

Jan Kitchel, Attorney at Law; Personal Injury – General: Plaintiff; Portland: My wife was on the American College of Trial Lawyers’ Access to Justice committee, and they called for volunteers to represent guys locked up on Guantanamo Bay. So I volunteered. We filed a habeas corpus case against George W. Bush, and when he was out of office it continued against Obama. My daughter, who at that time was not finished with college, became my legal assistant on the case—she’s now a successful lawyer. She and I made several trips to Guantanamo. My client, Younous Chekkouri, was from Morocco; he spoke French and [my daughter] was pretty fluent in French. Ultimately, he was released administratively from Guantanamo, back to Morocco, where he still lives.


Moon: I’d been in a firm for 24 years and I just wanted to go out on my own and see what it was like. My partners had done a nice job fixing up an old post office—a big, beautiful building—but it was expensive, so I decided to go out on my own.

Wong: In the late 1990s, a series of congressional hearings on alleged IRS abuses of power ended up with many heads rolling. The entire administration began to change and the job became less pleasant. I signed up with Greene & Markley in 1998 and stayed for 11 years but the job was killing me. I was the manager of my own tax and bankruptcy group, with incredibly complicated cases, I was serving on a couple different bar committees, I was training staff, I had young kids at home, and I was teaching. I was split every which way. Then everything got amplified by the recession. Hanging my shingle was an attempt to simplify and get back some of my personal life.

Grace Lee, Grace Family Law; Family Law; Portland: I always thought I would be in a firm environment. But as I got older, I found it more fulfilling to be self-directing and to have total control over the management of my cases and work environment.


Katherine Heekin, The Heekin Law Firm; Business Litigation; Portland: I learned bookkeeping from a CPA in Eugene, and my mom had been the daughter of a banker, so I knew not to get too far out over my skis. The best way to avoid that in the beginning was to sublet [an office] from a firm. My lease was month-to-month. They had the copy machine, the break room, the common area. I think they charged me for copies. I didn’t know where my cases were going to come from. I’d like to tell you I had a business plan. I had a back-of-the-envelope budget.

Lee: It wasn’t until after I had notified my partners that I was leaving that we coordinated together to notify the clients and give them the option of either coming with me or staying with the firm. It’s better for the clients that way. They’re already in a stressful part of their lives and they don’t need to be involved in any law firm drama.

Kitchel: I found a really nice space with several lawyers in a historic building. Setting it up is actually less expensive than you would think. I have a leather couch that I bought for $450. I bought a used wraparound desk and a couple of nice, wooden file cabinets that matched. Then you need a computer and scanner. I keep a paperless office so I don’t really need storage space. I don’t have any employees. I’m a fast typist. I do all the stuff I need to do without a legal assistant.

Fine: A friend bought a house in downtown Eugene that he was renovating into a law office for himself, and he needed another attorney. He had the copy machine, the secretary, the staff. I could just hit the ground running. At that time, in Lane County, we had the public defender service and an overflow list that the trial administrator assigned. I visited with a judge who put me on a panel specifically to defend the rights of people going through civil commitment. I also got on the regular panel with the trial court administrator. After about six months, I got my first retained client and slowly transitioned to more and more retained work.

Moon: I had a solid client base, I found a small office and the overhead was low. We bought an older home and fixed it up and practiced law in that for a period of time. Then we sold that house and bought an old bank in downtown Baker City. We’re renovating it right now. 

Wong: You need a telephone, a computer, a printer, a bunch of subscriptions, an accounting system, some malpractice insurance and hopefully some good assistants and you’re ready to rock and roll.


Heekin: The hard part in the beginning is knowing when to hire, because as soon as you commit to an employee you have to know what your cash flow will be. And that impacts what cases you take. When you’re only yourself, you have more discretion about when you get paid, or the terms by which you get paid, and you can take more risk. Once you have employees, you have to make payroll every two weeks, so you can get yourself into trouble pretty quickly.

Wong: The first three years were pretty tough. Between 2009 and 2014, I was a tax and bankruptcy lawyer in the middle of America’s worst recession. I spent most of my early years in private practice figuring out how to make the hard decisions of saying no to people.

Moon: I’ve got a pretty good legal assistant right now, but I’ve had some that were not good. Younger lawyers have good administrative skills. They can type their own briefs, file their own documents. I’m learning to do that, but I don’t have all those skills, and if somebody leaves me it’s a problem.

Heekin: I thought I had it figured out by 2008. I was doing great. And I made a mistake. I thought, “If you build it, they will come.” So I got into a five-year lease for a much bigger space. Right as I moved in, Bear Stearns collapsed.


Moon: I represented a woman who was accused of arson—burning down her restaurant for insurance money. We went to trial and got her acquitted. I represented a rancher in a horrible sex-abuse case right after I went solo. We were on trial for three weeks; he was convicted.

Fine: Two things happened my first month in private practice. The University of Oregon had a student legal services office funded by student-activity cards. The woman who had that job was going on maternity leave, so I was offered her job, a part-time position, and that guaranteed overhead every month. And because of my experience with public-safety labor unions, I was called by a local union who represented correction officers and said, “We have an inmate death and we need support.” I have been receiving a monthly fee from this union since 2003 to be on call. I was randomly contacted by the Consulate of Mexico, which asked me to represent Mexican nationals facing criminal charges. I realized the key to success was not depending on one faucet to fill my bucket.

Kitchel: I’ve had many cases involving caregivers. I like to call them the stripper-from-Vegas or the Argentinian-polo-player cases. A younger person marries an old person, and they begin to convince the old person that the kids are bad, the kids aren’t calling enough, all the kids want is their money. They make a will, with assistance from the caregiver, that cuts the kids out. Actually, one caregiver was from Vegas. She ended up marrying a guy who owned a large ranch and had three kids. He died after changing his will leaving everything to the new wife from Vegas. We sued on a will-contest claim and ended up settling and got the kids most of what they were after. 

Heekin: Dave Markowitz of Markowitz Herbold was very gracious. He gave me a soft landing. We partnered together on a very involved accounting malpractice case. It involved a hard-money lender and our job was to see if we could recover money for the business. It’s the kind of win you don’t want to talk about, because you win on negligence but you don’t get any damages.


Lee: After the first six months to a year, I felt pretty comfortable I had made the right decision. The phone was ringing. I realized there would always be work out there, so I didn’t need to worry about that part.

Heekin: I have a virtual office now. Three years ago, when my lease was up downtown, I decided it wasn’t necessary. By then, there were these co-worker spaces, so there are meeting rooms where I could meet with clients as necessary or take depositions. As we’re all evolving in this COVID world, I might revisit having a collective meeting space.

Kitchel: Arbitrations and mediations are all conducted via Zoom. I’ve had two mediations in person during the pandemic, just because the people wanted to be in person and they had really large conference rooms, so we could sit far apart from each other. I’m on the second floor of this historic house and there’s no one else on that floor. We wear masks when we go out in the hallway and chat with people.

Fine: I maintain my downtown office space but I’m working from home now. I have two horses and two goats and a dog and a cat. I live on 10 acres.

Lee: Certainly being solo, or self-employed, is more stressful. But I don’t know that your job is any more secure if you’re in a firm that ends up having to lay people off—including you.

Moon: I used to be acutely aware of how much money I had or how much money the firm had. Now my wife doesn’t even like to talk to me about it. So long as bill collectors aren’t knocking on the door, life is good.


Lee: Anybody can [hang a shingle], as long as they do the prerequisite preparation and research. 

Heekin: When you form your own firm, you figure out your sweet spot—not just from the law side but the business and people side. You’ve got to figure out where your gifts are and where they’re not. 

Fine: I encouraged a friend who left public defenders. I pointed out what the overhead could be and how it works and where cases would come from. She’s now a quite successful attorney in private practice as well.

Moon: Make sure you’ve got a good client base; then make sure you’re not overextending yourself as far as overhead goes.

Wong: I’m a mentor for the Oregon State Bar’s mandatory mentoring program. One thing I tell the young kids is, “You really need to work with an experienced, competent, ethical, financially responsible group of lawyers before you hang out your own shingle.” Because practicing law can be a dangerous way to make a living. There are lots of things that you can screw up. Intake and client selection are absolutely everything—the key to getting paid, the key to working with a minimum amount of stress.

Kitchel: I should’ve done it 10 years earlier.

So You Wanna Go Solo …

Advice from our solo practitioners

  • Do the prep and research
  • Figure out your sweet spot
  • Get a good client base
  • Watch your overhead
  • Be wary of long leases
  • Don’t forget to get paid

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