Creating a Satisfying “Second Act” in Your Legal Career

Attorneys are widely perceived as successful in life and many would affirm their satisfaction with their careers. But lawyers who can claim they “couldn’t be happier” are rare, and far more common are those who don’t take time to consider how making changes might yield greater satisfaction.

Some of you may remember the movie, City Slickers, starring Billy Crystal. He plays a radio ad salesperson who is going through a rough stage in his career. Like most, he complains to himself and others about his predicament, but unlike most, he is given a chance to reflect upon where he is in his career and where he’d like to go. The opportunity presents itself when he is asked by his son to talk to his elementary school class about his career. He begins his speech by saying, “value this time in your life. This is the time in your life when you still have choices. It goes by so fast.”

You Still Have Choices

I suspect no one reading this article is in elementary school, but Crystal’s advice is as applicable to practicing lawyers as it is to a ten-year-old. No matter at what stage you are in your legal career, you “still have choices.” Many lawyers are simply too busy, cynical or fearful to think about how they could create a more satisfying career. Even though we’re trained to plan out the most complex deal or litigation imaginable, few attorneys intentionally plan their own careers. Rather, when an opportunity presents itself, we take it and hope for the best. If all goes well, the comfort zone that’s created makes it difficult to want to change. If it doesn’t work out, we look for another job, hoping the next one works out better.

There’s a more proactive way to weigh and implement choices. With some careful planning and a bit of luck, you can create a satisfying second act at any time during your career: as a first-year associate or as a senior partner thinking about the best way to wind down and plan your retirement.

Attorneys searching for a second act want to do something different, more satisfying, than what they’re doing now. Some simply want to enhance their existing practice by finding a better mix of clients, others want to add a new practice area to what they already do, others seek to practice the same type of law in a new environment, and others want to stop practicing altogether. In short, a second act can range from tuning up what is basically working well to trading in for a new model.

Is It Time?

Lawyers by nature tend to be highly analytical. When making any career change, large or small, they tend do so only after consciously or subconsciously answering four simple questions. 1) Why do I need/want to make a change? 2) What do I want to do next? 3) How can I make the change? 4) What are the costs of the change? When the sum of the why, what, and how exceed the perceived costs, it’s time for a second act. In other words, for change to occur, one needs a good reason to do it, have an idea of what the change would be and how to achieve it, and finally, believe that the risk of the change is worth the associated costs. Let’s look at each of the four questions more closely.

The “Why.” The initial question is why even consider a second act? Three reasons tend to drive career changes. The first is dissatisfaction, which can take many forms including boredom, stress, poor work/life balance, not making enough money, or lack of job security. Second, some lawyers enjoy their practice, but want to make sure they maintain momentum, not lose their edge, or even better, take their practice to a more successful level. Finally, change is driven by personal or professional circumstances. On the personal side, perhaps a child has been added to the family, or an elderly parent needs more personal care. On the professional side, the most typical change is losing a job. Whether the reason for termination is performance-related doesn’t matter. Change must occur if you want to continue to earn a living.

The “What.” Once there’s a reason, you need to determine what’s next—to articulate a goal. If you just lost your job, the goal is easy; you need another one. It may not be easy to find a new job, but the goal is clear.

If you’re employed, the goal may not be so obvious. You may have a vague feeling that you want to take your practice to a higher level; perhaps you’re bored with your practice; or maybe your work/life balance feels out of whack. Creating tangible change under these circumstances requires honest self-assessment. Ask yourself, what do I really want to do? Or, what really matters? What motivates me? What are my passions? What’s meaningful to me? What do I enjoy doing? What don’t I enjoy? How do I want to balance my time for personal, professional and community activities? Or try asking yourself this question: What do I want people to say about me at my retirement dinner or funeral? Once you have some answers, consider what has to change.

Of course, there is more to goal-setting than lofty aspirations. You must have the ability to perform the second act. Again, honest self-assessment is key. Do I have the talents or skills required?

If you are exceptionally self-aware, goal-setting usually can be accomplished by putting aside time and thinking through the questions posed above. Others may find professional assistance helpful in identifying goals. A coach or counselor can be particularly helpful in probing subjects or eliciting answers to tough questions that people would rather avoid. Such professionals also have access to a variety of formal assessment tests, such as the Strong Interest Inventory, Myers-Briggs Type Indicator, and California Personality Inventory that can yield insights to help you identify your goals and skills.

The “How.” Once you have a reason to change and a goal to achieve, the next question is how to achieve it? (See the sidebar for a list of potential “second acts” you might consider.) Reasons and goals are necessary, but without ideas on how to accomplish them, you’re stalled. Two words familiar to most attorneys describe the “how” component of creating your second act: due diligence. This is the time to determine whether your goal is realistic. Are there opportunities for what you want to do? Can you make enough money? Start by doing basic research on the internet. Then, get out and talk to people. Chances are very good that someone you know, directly or by association, has gone through a similar career realignment. Meet with them and have the conversation. You’ll find that acquaintances and strangers alike are more than happy to share their experiences with you.

If, after conducting due diligence, you still believe your idea has potential, what’s next? To borrow a phrase from Nike, “Just do it.” If you’re currently out of work and seeking a position in a similar environment or practice area, start networking and interviewing for your second act.

If you are currently working, your path to a second act can be more sequential. Keep doing what you’re doing, but build a bridge to a new possibility one step at a time. You’ve probably “sequenced” in your career already without even realizing it. Think about the first time you were exposed to a case in a new practice area that you found a pleasant diversion from your regular caseload. Did this experience prompt you to shift your practice into the new area? People who sequence under a circumstance like this aren’t consciously seeking a major career change. They’re presented with an opportunity to test out, or perhaps they’re even forced into working on a new case, and are pleasantly surprised by how much they enjoy the new practice area.

But how many of you have ever “sequenced” proactively? That’s where you seek out an opportunity to try something new. You don’t dive head-first into anything, but rather put your foot in the water to see if you like the way it feels before plunging in. You can try moonlighting, pro bono work, board work, community service, Bar activities, and temporary assignments. By sequencing this way, you can you can see whether something new fits before abandoning what you’re presently doing—maximizing your chance of creating a successful second act.

The Costs. The final consideration before making the big change is to weigh its costs. The price of your second act must be perceived to be worth the attendant risks. If the costs are too high, the status quo remains an option. Obvious costs of change include the time and effort to pursue a change. Your second act could require a financial sacrifice or the loss of prestige. What if it doesn’t work out? Can you handle failure? Furthermore, there are emotional costs to consider. For many, their second act will feel like a roller coaster of emotions including excitement, fear, uncertainty, doubt, and anxiety. It can be confusing as you lose one identity and create a new one. Initially, you may feel out of place since many of your working relationships will change—your clients, peers, mentors and network. Lawyers typically underestimate the softer side of change. Don’t. Make sure you have a support system of family, friends, and professionals who can help you navigate the bumps in the road that accompany change.

Now What?

As Yogi Berra once said, “When you come to a fork in the road, take it.” It’s now time to decide if you want to pursue a second act. If you have a reason to change, a goal and a way to achieve it, and the sum of those three components exceeds your perceived costs of change, it’s time to get going. Create an action plan with goals that are SMART: Specific. Measurable. Action-oriented. Realistic. Time-sensitive. Start to think about the obstacles you might face in achieving your goals and how you’ll get around them. With or without the assistance of a professional, if you are patient, flexible, and disciplined, your second act could earn a standing ovation.

Mark Twain once remarked, “Twenty years from now you will be more disappointed by the things that you didn’t do than the ones you did do.” Perhaps now is the time for your second act. Chances are, you won’t be disappointed.

Potential “Second Acts”

Have trouble visualizing alternatives to what you are doing now? Here’s a sampling of potential second act options to help you formulate your goals:

• Take a sabbatical. If you remember, Billy Crystal came back from the cattle drive in City Slickers reenergized and told his wife, “I’m not going to quit my job. I’m just going to do it better.” He needed only a new adventure for a few weeks to make him appreciate what he had.
• Enhance your existing practice. Maybe you’re satisfied with your choice of practice area, but would like to become more successful—increase the number of clients with interesting cases. In your second act, you’ll be more focused and disciplined on business development.
• Switch environments. In this case, you might be satisfied with your practice area, but you’re not happy in your current location. Is the culture and size of your law firm right for you? Should you consider going solo? What about inhouse at a corporation or for the government?
• Modify your practice. You like your firm, but perhaps your caseload lacks variety. Look for opportunities to help out on a case outside your area of expertise. Having one or two cases that are not a part of the normal routine may be all that is required to refresh your act. Although it may seem counterintuitive, getting out of your comfort zone will make your practice a more comfortable one.
• Work part-time. This option usually is associated with working moms, but more fathers are considering working part-time. In addition, look for more baby boomers, both men and women, to work part-time rather than abandon their practice altogether when they reach retirement age.
• Stop practicing law. For litigators, a popular second act is to become a third-party neutral and take on a new role in the area of alternative dispute resolution. As inhouse corporate counsel, have you considered a business role at your company? Or, maybe you’ve simply had enough of the law and it’s time to become a celebrity chef!
• Rebalance. Here’s a second act that all lawyers should probably consider. I know or meet hardly anyone who is truly satisfied with how they juggle their personal, professional and community involvement priorities. In my view, no one can ever be completely satisfied because there is no perfect balance. However, it is the rare person who cannot achieve a better balance.