Episode 19-Canoeing vs. Whitewater Rafting-A Career Conversation With Jose Sierra

When I counsel lawyers on their careers, I always encourage them to get out of their office and network with other professionals.  Sitting at your desk, you can make lists of the things you like about your current position and the things you would like to change.  You can do an inventory of the skills you have and think about your values. If I’m working with an attorney on career satisfaction, I might also have them make lists of their professional and personal interests and think about the type of work environment that feels right. But getting away from your desk is very important when you want to gain perspective on your career.  Meeting with lawyers or other individuals who have the job you think you would ultimately like to have is invaluable.  When I was in college many years ago, the book What Color is Your Parachute was very popular. While the themes in the book may have changed (I haven’t read any of the 35+ annual revisions that have come out since I graduated) the basic gist of the book was to figure out what you like to do, what you are good at and then start pursuing a career that leads you in that direction. What I’ve learned since that time is that careers are not at all linear.  They meander back and forth and there is a lot of serendipity in how our professional lives progress. I speak to a lot of lawyers about their careers and I’ve noticed a pattern.  Many lawyers end up later in their careers in roles that they could not have predicted when they were just entering practice.  I would certainly say that has been true for my own career. My guest in this episode, Jose Sierra, is someone who epitomizes that career path.  Jose is a partner in the Boston Office of Holland and Knight.  I was recently having coffee with him and he said to me that for some individuals, career paths are like a canoe ride across a lake.  You chose a destination and then you start paddling to it. Jose then said that his career has been more like whitewater rafting. You eventually reach a destination, but it may not be the destination you originally set out to reach and you may not have been able to predict how you would get there. I thought that was a great metaphor and invited him to be on Counsel to Counsel to talk about that. Jose is a Boston attorney who focuses his practice in the areas of white collar criminal defense, government investigations, healthcare fraud and abuse, the Foreign Corrupt Practices Act, compliance, and business litigation. He is well-versed in the areas of healthcare fraud and life science compliance and has advised healthcare and pharmaceutical industry executives, audit committees and corporate board directors on legal, employment, compliance and business strategies, including due diligence advice in connection with corporate acquisitions.  Prior to joining Holland and Knight he was a partner at a large IP boutique and then at a small Boston firm.  He began his legal career as a clerk for the 5th Circuit and then as an Assistant US Attorney in New Jersey.  Before entering private practice, he served as senior vice president and chief ethics and compliance officer for two pharmaceutical companies.  In this episode, he talks about how he has always sought opportunities for career growth and how that has taken him in many unexpected directions.