September marks my 35th year in the legal profession (and 37 if you count being a summer associate and clerk during law school). I have been fortunate to experience the profession from many vantage points, including clerking for a governmental agency, being an associate and partner; working in-house, which included two general counsel stints, and, for the past 18 years, working as a recruiter and consultant for a wide range of law firms, corporations and individual lawyers.

Along the way, I have worked with or otherwise know lawyers who span the spectrum, from current law students to the most experienced practitioners. I often inquire as to the paths that lawyers have taken in their careers and some of the observations they have about the journey.  One particular aspect I have asked others about is what surprised them the most about the practice of law.

In this two-part series, I will share the most common answers to those questions, with a focus on responses of those of my vintage or older. It is my hope that this longer-range perspective may be especially helpful to those who have many more years in the profession ahead of them.

1. You Need to Be Comfortable With Selling

I recall sitting in an orientation class just before our first official day of law school. A professor asked why we wanted to be lawyers and one intrepid soul blurted out: “because I want to be a professional who can focus on my work and doesn't have to deal with sales.” The word “sales” dripped off his tongue as if it were laced with poison, as the contempt he had for that facet of business reverberated quite loudly.

At that time, in the early 80s, you technically could not only get by, but could have a great career, even if you didn't excel in sales. Many law firms were fueled by institutional clients that provided huge swaths of revenue, which essentially meant that you could make partner and would have veritable lifetime security if you were a good lawyer and didn't step on any political landmines. Similarly, in-house lawyers had a more traditional arm's-length relationship with executives and could practice much like they did in law firms.

As time passed, those paradigms were turned upside down. Law firms now fiercely compete for revenue, and, if you want to become an equity partner, and truly want security, it behooves you to become a business-getter. While in-house lawyers don't have to ask for business, they do have to market their services throughout the company and thus engage in many of the same activities as their private practice brethren with respect to selling.

I used the word “technically,” above, because another fundamental precept, which has become much more apparent in recent times, is that lawyers are “selling” almost all the time. How you present yourself (and your organization) comes into play throughout the day—even when you are not working—as others are continually forming impressions of you that go a long way toward your success or failure as a “sales” person. The days of being able to shield yourself from “sales,” by holing up in a library or closing your door throughout the day, are over.

2. The Path Not Taken Is Most Lawyers' Biggest Regret

Jackson Brown Jr. is credited with saying that: “Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did do.” Many lawyers have told me that, when they were coming out of school, they would have predicted that their biggest regrets would have been mistakes they made that led to some type of defeat—losing a trial or key client, failing to land a major deal, not getting the leadership position they wanted, etc.

In actuality, that has not been the most common refrain. Rather, it has repeatedly been emphasized that they rue what they decided to pass on—whether that was a job opportunity, chance to take over a department, firm or company, make a shift in their practice, more ardently pursue a client, or any number of other similar omissions.

Sometimes the failure to act was driven by inertia that was so gripping that they felt like David Blaine chained inside of a box. For others, it was a matter of being so busy—and looking for the next assignment, case, or deal—that they couldn't step back to see opportunities that were sitting right in front of them. And, for quite a few, that four-letter word, F-E-A-R, was at the root of their indecision, and, with the benefit of hindsight, especially pained them. A key reason for that is that, over the course of their career, they had failed many times, and picked themselves back up—the fear that scared them at other times, particularly early, should not have stopped them, as they now know they would have been able to bounce back from a setback.

3. Your Career Can Be Significantly Impacted by Winning or Losing the Practice Area Lottery

Many lawyers start, and stay, in a practice area simply because it happened to be the department that had an opening when they joined a law firm, company or other organization after graduation. If you didn't grow up in a family in which someone was a lawyer, or otherwise didn't have a mentor or other person who could guide you, it was akin to engaging in a game of chance, that has huge consequences, if you accepted a placement, and didn't help drive, if at all possible, the decision as to what area of law you wanted to practice and spend thousands of hours a year doing so.

Unless a firm rotates you through practices—which not as many do—and thus affords an opportunity to more deeply experience a practice area and its fit, or not, the risks of being in the wrong practice are magnified. If such a misfit occurs, many will accept it and will attempt to slog through it, as they may think that they are the root cause of the problem or that things will get better over time, which rarely happens. The deeper that one gets in, the harder it is to turn back, particularly if doing so entails being docked a year or two of experience along the partnership path.

Even if the roulette wheel stops on the right color for you, the number may be wrong for a novice lawyer. For example, consider litigation. Some may be much more cut out for consistent, higher volume practices (such as products), rather than longer-tail complex commercial cases that pop up much less often, but, nonetheless stay trapped in the discrete area that doesn't fit them. The answer is to conduct better due diligence, if you can, at the outset, and, when it becomes apparent that there is a mismatch, make a change, even it entails a momentary step back. Over the longer arc of your career, that will be a very small fragment of time and not the major regression it seems then.

4. In-House Is Not Automatically a Panacea

In the 80s and 90s, in-house was perceived as a great option, if not the holy grail, as lawyers often worked fewer hours, received very good work, had good job security, were immune to having to “sell” (as discussed, above), and still were compensated fairly close to what their peers were making in private practice.

I worked in-house during part of that period, and can attest that many of those elements were in play. I loved my experience, especially being intertwined in the business of a company, as that was very fulfilling. Once again, though, as time passed, things changed with many in-house positions.

For instance, consider hours. With the advent of laptops, smartphones and our always on-demand world, many in-house lawyers have been as “on call” as those in law firms. And, to make matters worse, some in-house departments started requiring their lawyers to fill out time sheets, an anvil that they thought they had shed when leaving private practice.

Increased M&A, and much more turnover at the CEO and general counsel level, have also meant a lot less job security in-house. I can personally attest to that when one of my companies was sold and I, along with the rest of our management team, learned what the words “corporate synergies” really mean.

The upshot is that the differences between in-house and private practice, which do exist, are not as great today. The gap in compensation, especially if you are a rainmaking partner, has mostly widened in favor of private practice, also. The calculus is thus more complex than one may realize, especially for more junior lawyers who are more prone to quickly decide that private practice is not for them. They may be right, but the decision requires much more deep thinking and analysis than it ever has.

5. Leadership Really Matters

Back in the day, companies with good products/services almost seemed to run themselves, as we had not yet entered the era of the celebrity CEO. It was similar with law firms, particularly since many had large institutional client bases, which had been with firms for decades, that kept them humming, even in the toughest of times. A quiet leader who rose through the ranks was often a perfect managing partner for such a firm.

Leadership, especially in private practice, has a profound influence today. The best leaders, particularly at the large-firm level, are facile when dealing with the press, are able to garner support and keep things stabilized inside their firm, excel at recruiting, which is crucial for maintaining and growing top-line revenue, have strong strategic and financial skills, and are not afraid to make hard decisions and take risks.

That is quite a package of skills for a lawyer and it shouldn't be a surprise that there is a small universe of persons who have all  those attributes and excel at leading. The impact of poor leadership, if not “ho hum” management at the top, is significant today, as change happens much more quickly and the consequences can be telling. Look no further than the demise of former bellwether firms or how quickly today firms are getting eclipsed by competitors who had trailed them for many years. In many cases, leadership is a key contributing factor and has taken on considerably more importance than it did decades ago.

Frank Michael D'Amore is the founder of Attorney Career Catalysts, www.attycareers.com, a Pennsylvania-based legal recruiting and consulting firm that focuses on law firm mergers and partner placements. He is a former partner in an Am Law 200 firm, general counsel in privately held and publicly traded companies, and vice president of business development. He can be reached at [email protected].