Modern solo practice — 25 years in

I started practicing law in 2001. The internet existed, but case law research still happened mostly in books or through dial-up access to Westlaw at $14 a minute. Court filings were paper. Service of process meant physical service or, on a generous interpretation of the rules, fax. Most of the practice management technology that exists today did not exist; the firms I knew tracked matters on paper calendars and yellow legal pads.

Twenty-five years later, the practice looks transformed. Case law research is instant and unlimited. Court filings are electronic. Service is often by email. Practice management software, electronic discovery, AI-assisted drafting — none of it existed when I started, all of it is part of an ordinary day now.

The technology has changed almost everything about how I do the work. The work itself has changed almost nothing.

This is an essay about the parts of solo practice that don't change, the parts that have changed more than people realize, and the parts that are about to change again. After twenty-five years, what I think I have learned about practicing law on your own.

What hasn't changed

The work of a litigator, at its core, is the same now as it was in 2001 and the same as it was in 1971. You meet a client whose problem the law might address. You evaluate whether the law can actually address it. You collect the facts, develop the theory, and translate the theory into the language and procedures the court system requires. You navigate the procedural environment until you reach a result — settlement, judgment, withdrawal, or trial. You bill the client appropriately and you maintain your professional standing for the next matter.

Every part of this is interpersonal, judgment-laden, and dependent on the lawyer's individual professionalism in a way no technology can substitute for. The client's trust is earned by the lawyer, not by the platform. The case theory is constructed by the lawyer, not by the AI. The settlement is negotiated by the lawyer. The trial is tried by the lawyer.

The parts of practice that don't change are, in my experience, the parts that make it worth doing. The parts that have changed are the parts that used to make it difficult to do well.

What has changed more than people realize

The visible changes — research speed, electronic filing, AI drafting — get most of the attention when lawyers talk about how practice has evolved. The less visible changes have, in my judgment, mattered more.

Access to peers. In 2001, a solo practitioner could be functionally isolated. The peer group consisted of the lawyers you knew in your physical community. If you had an unusual question on a specialty area, you had to know the right person to call, and if you didn't, you spent days finding them. Today, a solo practitioner is connected to a much broader peer network through bar association listservs, practice-specific online communities, conferences that are reachable on a budget, and informal networks that operate at scale. The isolation problem of solo practice, while real, is much smaller than it was.

Cost of starting. In 2001, starting a solo practice required a real estate lease, a phone system, a paralegal, a paper library of state-specific practice guides, and several thousand dollars in initial software licenses for the limited tooling that existed. Today, the entire infrastructure of a solo practice can fit on a laptop. The barrier to entry has collapsed.

Client expectations. Clients in 2001 expected to communicate with their lawyer by phone and to come into the office for meetings. Today, clients expect text-based communication, electronic document signing, video meetings, real-time updates, and an online portal to view case status. The lawyer who hasn't adjusted is competing with lawyers who have.

Substantive sophistication available to solos. This is the change that I think has been the most consequential. In 2001, the substantive sophistication a solo could deploy was limited by what one person could keep current on. You picked a practice area, you developed depth there, and you turned away matters outside it because you couldn't compete with the larger firms that had the cross-disciplinary depth. Today, a solo can deploy substantive sophistication that approaches what a much larger firm offers — not by being a polymath, but by using infrastructure that gives access to the depth without requiring it to be in your head.

The change in available sophistication is the change that has done the most to level the playing field between solos and large firms. It is also the change that is most underway. It will keep going.

The pressures that are real

Solo practice has always been harder than it looks from the outside, and most of the hard parts are not the parts that get talked about.

The hardest part, in my experience, is the absence of a backstop. When you make a mistake at a large firm, there is a partner above you who catches it, a paralegal who covers for you, an associate pool that can absorb the work. When you make a mistake as a solo, the mistake is yours alone. The malpractice exposure is yours alone. The disciplinary exposure is yours alone. The professional consequences are yours alone. This is a lot to carry, year after year.

The second-hardest part is the constant context-switching. In a single day, a solo handles client communication, court appearances, document drafting, depositions, settlement negotiation, billing, bookkeeping, marketing, and operations. None of these tasks is hard in isolation; the difficulty is the cumulative cognitive load of switching among them. Burnout in solo practice is not from the work being hard. It is from the lack of a single coherent focus.

The third-hardest part is the financial volatility. Solo income is matter-driven. A good month can be followed by a bad month for reasons entirely outside the lawyer's control. Building financial reserves takes years, and those reserves can be depleted by a single bad case or a delayed payment. Solos who do not understand their cash flow do not survive.

The fourth-hardest part — and the one that has gotten worse rather than better over the last decade — is competitive pressure from larger firms that have access to better infrastructure. The associate at a fifty-attorney firm with subscription-tier research databases, integrated case management, and now AI-assisted drafting can match the productivity of a solo three times her experience. The solo has to compensate either by working longer hours or by adopting the same infrastructure. The infrastructure has historically cost more than solos could afford. This is changing.

What I have learned about doing it well

Twenty-five years in, here is what I think I have learned about practicing law on your own and doing it well.

Pick your work carefully. The matters you take define the practice you have. The temptation, especially early in solo practice, is to take what comes. The lawyers I know who have built sustainable practices over decades are the ones who learned to say no to matters that didn't fit, even when the income was needed. The wrong matter is more expensive than no matter.

Invest in the infrastructure that returns the investment. Some technology saves time and lets you bill more matters per month. Some technology makes you a better lawyer on the matters you have. The first kind is helpful. The second kind is foundational. The infrastructure that increases the quality of your work compounds over decades; the infrastructure that increases your throughput maxes out at the limit of your bandwidth. Most lawyers underinvest in the foundational kind.

Document your processes. Twenty-five years in, the most consistent regret I hear from senior solos is that they never wrote down how they did things. They have decades of institutional knowledge locked in their own heads. When they retire, the knowledge retires with them. Younger lawyers who could have learned from it never do. Writing down your processes — checklists for client intake, templates for matter types, standard language for engagement letters — is a low-glamour investment that pays back over the entire arc of a career.

Maintain the boundary between professional and personal. Solo practice rewards intensity. The lawyer who is willing to work nights and weekends, who is always reachable, who takes the calls in the evening, will outperform the lawyer who isn't, in the short term. Over thirty years, the lawyer who maintained a boundary has the longer career and the better professional standing. The lawyer who didn't burns out, or worse, doesn't burn out and instead becomes the lawyer no one wants to refer cases to because every interaction is operating on too little sleep.

Be useful to other lawyers. The solos who get the best referrals are the ones who refer well to others. The economy of legal practice is more cooperative than it looks from the outside. The lawyers who treat colleagues as competitors get treated the same. The lawyers who treat colleagues as part of a broader professional community get the referrals that build their practices.

Stay current on the law. This sounds obvious. It is not obvious in practice. Most solos, fifteen years into practice, are operating on the law they learned in their first five years, plus the ad hoc updates they pick up through their actual matters. The lawyers who deliberately stay current on the broader developments in their practice area produce better work for clients and avoid more avoidable mistakes. CLE is a floor, not a ceiling.

What is about to change again

Solo practice is about to change again, and the change is roughly the same shape as the change from 2001 to 2010. Then, the change was the internet making solos competitive with much larger firms on research and communication. Now, the change is AI infrastructure making solos competitive with much larger firms on substantive depth.

The lawyers who adopt the infrastructure that becomes available in the next three years will, in my expectation, run practices that are substantially more sophisticated than the practices that were possible for solos five years ago. The work they do will rival what their large-firm counterparts deliver, on a fraction of the overhead, with the autonomy and client relationship quality that solos have always had.

The lawyers who don't adopt the infrastructure will, I think, find themselves in a position they have not been in before — outcompeted on substance, not just on throughput. The competitive pressure on solos from larger firms with better tooling will keep increasing. The way to respond is not to work harder. It is to use the tooling.

I built Discover Docket partly with this in mind. The platform is meant to be the infrastructure that lets solo and small-firm litigators run practices that look and operate like much larger firms' substantive output, without the overhead that has historically made that impossible. It is not the only platform that will do this, and it will not be the only path forward. But the broader shift is real, and the lawyers who position themselves for it are the ones who will define solo practice in the 2030s.

Twenty-five years in, I am still convinced that solo practice is the best way for a lawyer to do this work. The autonomy, the client relationships, the absence of large-firm politics, the alignment between your professional values and your daily decisions — these are real and they are valuable. The hard parts are real too, and they always will be. What is changing is what tools you can use to do the work, and how those tools are letting solos do work they previously couldn't.

If you are at the beginning of solo practice and reading this, the practical advice I would give you is this: invest in the infrastructure. Spend the time to learn the new tools. Build the foundation now, while you have the bandwidth to build it deliberately. Twenty-five years from now, the practice you will have is the practice you built in the early years.

Read more from The Docket →

See what we built at Discover Docket →