15 Painful Moments of Running a Law Practice (and How to Feel Better)

There are moments of great joy in the practice of law.

There’s joy when we win. There’s joy when we lose, as long as we gave it our best shot.

There’s also joy when we know we made a difference in the life of someone who needed help. Being a lawyer can be pretty awesome sometimes.

Many lawyers experience these moments of joy without running their own law practice. Running a practice can be challenging and painful. It’s not for everyone.

When times are good, they’re often really good. They are high-five slapping, fist-bumping good. The adrenaline highs are intense, especially if you work for a litigation or transactional firm, or a firm navigating a course through bureaucracy.

Sometimes, practicing law is even better than what they show on TV. The people aren’t usually as attractive, but the taste of victory can be very sweet.

Don’t get me wrong: Running a law practice is not all rainbows and sunshine. Sometimes it’s dark clouds and disappointment. Sometimes it’s depressing and demoralizing.

When you feel down, defeated, and unsure if you should continue, remember that you aren’t alone.

Running a practice is hard for all of us at some time. We’re good at hiding it, though, aren’t we? We’re good at keeping it all under wraps. We’re good at keeping our emotions private, but we still feel the distress, the unhappiness, and the tension percolating under the surface.

Lawyers are good at looking good while feeling bad. We’re good at appearing detached, objective and neutral. We’re trained to deconstruct, disconnect and analyze. We smile pleasantly as the world around us unravels. “Thank you, your honor,” we say, with a smile, as our objection is overruled.

We tend to assume it’s just us. We see other lawyers who look good and smile big, and assume they feel great. We worry that we’re the only ones who feel stressed or depressed.

But we aren’t alone.

No matter how charmed the life of the lawyer down the hall may appear, that’s not always reality.

Our unwillingness and inability to show pain to others, to be open and vulnerable, doesn’t mean we don’t feel it. The lawyer down the hall, and the one down the block, and the one sixty stories above all feel that pain sometimes.

Often that pain isn’t fleeting, either. It can linger. Sometimes it just won’t relent. Many of us don’t feel as positive about our work as we would like.

The Most Painful Moments of Running a Practice

As you run your practice and serve your clients, you’ll endure plenty of moments that trigger that pain.

Some moments are small. Some are big. All are painful to a greater or lesser degree. Some allow for quick recoveries. Some take a while to banish. Some pain will linger long after its trigger has passed.

I’ve been lucky to skip a few, but I’ve also experienced many of them.

Today I want to run through the list of the most painful moments of running a law practice.

1. You’re not in charge

We open our practices, in part, to give ourselves control over our lives. Owning a business is supposed to create freedom, right? We want to set our own schedules, take time away whenever we please, and make our own decisions in regards to how much we work.

But then the moment comes where we cancel the family trip, skip the special meal, or disappoint the loved one on that special day. Our schedules aren’t in our control. Reality strikes the moment we realize that we aren’t in charge.

It’s painful, but we accept it. We accept that other parties (clients, judges, other attorneys, etc.) have a great deal of control over our time. We want to believe that we’re calling the shots, but that first awareness of our lack of control can be shocking.

2. The client hired another lawyer

The initial consultation went well. You really clicked with that client. She seemed ready to move forward. But suddenly she requests her paperwork returned. She has hired someone else. It’s painful, especially because you don’t like the lawyer she selected. This happens time again and time again, and it’s always painful.

3. The friend who referred to someone else

You thought you were best buddies. Then she sent her close friend to a different lawyer for a matter you would have handled well. You try to console yourself. “She doesn’t understand my practice area,” you say. Or maybe: “She didn’t realize I could handle the case.” But you know, deep down, that she choose someone else because she didn’t trust you with the matter. It hurts.

4. The client’s check bounced

Don’t you hate getting these notifications from the bank? One step forward, two steps back.

It’s hard enough to get a good client in the first place. Now you have to go back to the client, explain the situation, and convince them to make a new payment. It’s unpleasant when your victory is snatched away like that.

5. Getting fired by the client

I don’t like being fired even if I hate a client. I never liked being dumped by girlfriends either.

Usually, being fired by a client is a fine way to end a bad relationship, but it’s never easy. It causes us to replay the entire representation over and over, wondering if we should have done something differently. There’s no happy, upbeat way to re-frame being fired. It’s just awful.

6. The negative online review

Reviews are everywhere – Facebook, Google, Yelp, Avvo, and more. It’s thrilling to get five stars.

Negative reviews, however, are tough. They punch a hole in the vulnerable spot where we feel embarrassed. They make us worry about what others will think and how that thinking might impact our growing business.

Sometimes a negative review can be removed, repaired, or responded to adequately. Much of the time, however, we’re forced to adjust to the reality of that nasty review sitting out there indefinitely for the entire world to see. Ugh.

7. The client turns on you

It’s usually someone you like. You identify with them. You trust each other. The relationship is humming along, work is getting done, and progress is being made.

Then out of the blue, it’s all your fault. You are blamed for everything that’s gone wrong. You trusted them, but their outburst undermines your trust in yourself. Suddenly you find yourself turned upside down, confused by the unexpected torrent of a client’s displeasure.

Maybe they were emotional, irrational, or triggered by something in another part of their life. It’s hard to know why it happens, but it’s always unexpected. You can tell yourself that emotional swings are the nature of the game, but it still hurts.

8. The staff member quits

The departure of a staff member is tough. We get emotionally attached to people, so it’s hard to watch someone leave. It’s even more painful when that person has become a repository of knowledge. We rely on our employees, which often turns into dependence.

Occasionally I encounter a lawyer who is tracking down a former employee to figure out how to locate or access certain data. The former employee may be the only person who knows the ins-and-outs of the practice. Growing dependent on an employee and then losing him/her creates pain that’s more than emotional. It can impact you financially and cost you a great deal of time.

9. The associate quits

This is a punch in the gut. It’s especially hard first time.

We often see ourselves in our associates. We give and we give, and they pay us back by giving two weeks’ notice (if we’re lucky). It hurts.

This gets easier if you keep hiring and training associates. You’ll learn to make better selections, you’ll improve your management style, and some will stick around. But it’s never easy when they leave. It feels like rejection, because it is rejection.

It’s hard to accept that you haven’t created a utopian law firm that no one would ever leave.

It’s even worse if your associate was poached by someone you considered a friend. Friends don’t steal their friend’s associates.

Some will argue they aren’t “stealing.” They’ll say that your associate would have left anyway. They frame it like they’re doing you a favor by clearing out the flammable underbrush that would have ignited into a dangerous fire.

Those rationalizing lawyers are not your friends. In fact, those lawyers don’t actually have friends.

10. Your first grievance

The grievance notification arrives and the dread, fear, and anxiety settles in. This kind of pain isn’t the quick, stabbing pain like other causes. This pain is slow, throbbing and unrelenting. It lasts for months and it creates a special form of dull misery.

Hopefully, your grievances are eventually dismissed and the weight on your shoulders dissolves. The first grievance is more painful than any others. Sadly, you’ll never forget your first.

11. Paying everyone except yourself

You might anticipate this moment all month, but it truly comes into focus when you’re signing checks.

Paying everyone else, but being unable to pay yourself, makes you want to bang your head against the wall. You’ve built a business with clients and a team. How is there nothing left for you?

Unfortunately, not being able to pay yourself is usually the result of a confluence of other painful events. It might coincide with a client’s bounced check or a referral sent to someone else. It’s a painful moment stacked on other painful moments, and it can be excruciating.

12. Watching someone else pass you by

We’re competitive. That’s an asset and a liability. We love winning and we find it motivating. We hate losing. While it sometimes energizes us to try harder, other times it brings us down. We’re not big fans of watching our peers hit the target while we toil away trying to make progress.

Winning all the time isn’t realistic. Every winner loses some of the time. Knowing that, however, doesn’t make it less painful. There will be others who move faster, go farther, and win more than us. There’s not much we can do except keep trying.

It hurts to feel like we’re giving it our best, but still fall short. It rolls around in our brains. We try to explain it to ourselves. Sometimes there aren’t any good answers.

13. Not meeting payroll

I have met payroll more than 600 times. It hasn’t always been easy. I’ve never had to ask my team to wait a few days for funds.

But it’s been close sometimes. Very close!

While I’ve never personally experienced the pain of missing payroll, I’ve dreamed about it frequently. In my worst dreams, I’ve felt the embarrassment, heard the rumors around the legal community, and endured a loss of trust with my team. Those dreams wake me up.

I have been lucky to have pulled it off so far. I hope the streak continues. I’m not prepared for the pain.

14. You know it’s not for you

Some lawyers learn that they’ve landed in the wrong role.

It’s not obvious at first, but they see it around the edges. They don’t like the marketing. They don’t want to make hiring and management decisions. They don’t enjoy the technology or the financial management. Some just want to practice law. Others recognize that they don’t want anything to do with the law at all.

The warning signs are important. They serve as signals that this life isn’t for you. When you’re not happy, experiencing depression, unable to support your family, seeing the credit line balance grow, unable to sleep, stressed, unable to eat, engaging in unhealthy behavior, etc., then it’s time to take note and take action.

Treatment is valuable and may solve the problem. But sometimes it’s essential that you move on and find another way to spend your time. This life isn’t for everyone. In fact, it’s probably not for many lawyers who are doing it.

The pain of acknowledging that you’ve invested years in a poor choice is rough, but it’s the first step in solving the problem if you feel the law isn’t right for you.

15. The death of the dream

Sometimes we have to give up. We’ve tried everything. It’s not working. It’s over.

And with that realization dies our identity. We’ve given up the thing that defines us. We told everyone we would be successful lawyers with our own firm, but now we’re not. Most importantly, we disappoint ourselves.

Letting go is painful. The pain pushes us to stay with things long after we should let them go. We keep pushing, even though we know it’s pointless and futile. It’s not easy to let go even after we’re absolutely certain that it’s over.

And then, one day, we let it die. It’s done, but instead of feeling worse, we feel better. It needed to die. With that decision, we find a new path and a new destination. Accepting the death of our old dream creates space for a new one.

Pain is Part of Our Game

Pain is part anything worth doing. Painful moments are part of the experience. They happen to us all. We’ve all been there and felt the distress. You aren’t alone.

For some of us, the pain halts our course. It begins to define us. It becomes the reason we didn’t achieve more, and the reason we change course. There’s no shame in letting pain change your course. Maybe a new one is better.

But pain doesn’t have to stop you or change you. You can manage it, overcome it, and learn from it. It’s possible to accept pain and push past.

If you decide to press forward, pain becomes just one of the many obstacles you’ll encounter. It forces you to act in different ways to achieve new outcomes. It teaches you new methods of responding to future pain and minimizing it.

You don’t have to just take it. You can proactively respond. You can increase your resilience and your capacity for handling challenges.

These are some approaches I’ve tried or considered. Some have worked for me and all have worked for many.

1. Meditation

Meditation is all the rage. I think it’s awesome and I do it (although not as often as I should).

There are apps, teachers, courses, retreats and other resources. The benefits are documented by scientists. If meditation does nothing other than insert a tiny bit of mental space between painful events and your reactions to them, then it’s done enough. A fraction of an inch of mental space provides the opportunity to respond differently than your automatic, off-the-cuff response.

Play with meditation. Experiment. Explore your brain and see if you can give yourself some relief.

2. Exercise

Like meditation, exercise has been studied extensively. The consensus? It works. It makes you more fit. It relieves depression. It elevates your mood. Why aren’t you exercising? It doesn’t matter. Put on your shoes (or go barefoot if you prefer) and walk, run, swim, bike, or pummel your imaginary client in the boxing ring.

3. Counseling

If the pain is really starting to wear on you, see a counselor. It wouldn’t hurt to go prophylactically since we know the pain is coming if it hasn’t already arrived.

Don’t be skeptical of counselors. Counselors (like lawyers) train for years to deliver most of their value by talking in a private room. You might doubt their value for the same reason your clients doubt your value. Just like your work, the value of a counselor is tough to identify on the surface. Value is in the education, training and process.

A highly trained counselor delivers value just like you. Seek out the help and accept it. It’ll make a big difference.

4. Change practice areas

Sometimes painful moments are more frequent, or the pain is greater, when you focus on a specific practice topic. Maybe there’s a personal connection that’s nagging at you. Maybe the clients remind you of your mother. Maybe the type of client is needy or difficult.

The solution might be to make a change. If executives piss you off, maybe you’ll be happier serving families. Sometimes changing your arena can change your attitude.

5. Find employment

Practicing law is hard enough without owning the law firm and managing the responsibility. Some lawyers are happier working for governments, businesses, or taking a role in someone else’s firm.

You can still practice law without having to own every client problem and without having all of the management/marketing/finance responsibilities.

6. Change careers

A legal education is applicable to many fields. You don’t have to practice law. Many lucrative occupations require logical, orderly thinking for solving complex problems. Being a lawyer isn’t your only option. In fact, many lawyers have moved to other fields and excelled. Use what you’ve learned, coupled with your experiences, to move in a new direction.

For some, changing careers involves going back to school. Most of us are pretty good at school and enjoy it. Some lawyers find themselves turning a passion or hobby into a new career or business. Some lawyers simply look for employment that generates income, and they find happiness with more free time away from work.

There are former lawyers doing everything imaginable and it’s not uncommon for them to find satisfaction away from the law.

You Are Not Alone

If the pain is wearing on you, there are options and solutions. You don’t have to tough it out. You can, instead, seek information, evaluate options, and take action toward a solution.

We’re good at solving problems for others. Sometimes, we need to solve problems for ourselves.

Most importantly – and especially when you’re mired in a particularly painful moment– remember one thing. You are not alone.

You are not alone. We all feel it. We all know the pain. We all feel it more than we let others see.

Sometimes it’s hard. Sometimes it’s overwhelming. Sometimes it’s not what you’d hoped for.

You really aren’t alone.