For as long as I can remember, I have been driven and achievement oriented. It started when I was six years old, playing tee-ball for the first time, back in an era when the score was kept, runs counted, and you didn’t get a trophy just for showing up. One game, I was so pleased with myself for hitting a double, but then Jamie Ditzenberger stepped up to the plate. He crushed the ball and rounded the bases (even as a six year old, I remember it being a spectacularly hit ball). It was so cool to cross home plate, high-five Jamie, and cheer with my teammates. Whatever that feeling was, I wanted to bottle it and drink it up in large doses. My drive has led me to some great success in life, but it has also been responsible for some of my biggest work and life challenges.

Why is it that so many smart, ambitious professionals are either less satisfied or less productive than they could be? Why is it hard for some high achievers to embrace risk, choosing instead to stay locked into old, safe routines? These are two of the questions a Harvard Business School professor, Dr. Thomas DeLong, answers in his book Flying Without a Net.

10 Obstacles to Professional Achievement

Here are 10 factors that can cause lawyers and other driven professionals to stall and hit a wall.¹

1. Getting stuck in repetitive tasks. Challenging tasks push and motivate lawyers. If work becomes tedious or repetitive, lawyers can become unmotivated or feel as though they’re falling behind their peers.

2. Not knowing what is urgent versus just important. When I was practicing law, a client of mine used to categorize the priority of his projects with this three-tiered system: nuclear, super-nuclear, and catastrophic. I laugh as I write this because I still don’t know what distinguishes one from the other. By the end of my law career, though, I could no longer distinguish between tasks that were just important and those that were urgent – I perceived everything as urgent.

3. Trouble delegating. Lawyers tend to have very high standards for themselves and others, which may make them reluctant to delegate. It takes a certain amount of vulnerability to hand over a task and trust that it will be completed to an acceptable standard.

4. Transitioning to leadership roles. Many lawyers are selected for leadership roles because they have shown that they are good at billing hours, a skillset that does not always correlate with leadership success. As a result, lawyers might find the transition to leadership difficult and either micromanage or continue to be an individual contributor while learning the ropes.

For lawyers who are new to leadership roles, there is help. Harvard Law School’s Executive Education program, for example, holds management and leadership courses throughout the year for general counsel and other high-level legal officers, as well as law firm leaders including early to mid-stage partners, senior law firm leaders, and leaders of firm industry-sector groups.²

5. Avoiding difficult conversations. Even though I teach people how to communicate assertively, it’s still tremendously difficult for me to be vulnerable and sit with the uncomfortable feelings that I know will result from having a difficult conversation.

But, here’s an example of why it’s important to have these conversations: Last year, I started collaborating and sharing ideas with two business colleagues with the goal of potentially starting a business together. After a few months, they decided to develop this business opportunity without me. That would have been just fine, but they decided not to tell me they were excluding me, and I found out about their venture launch via a social media post. It’s hard to maintain trust and friendship under those conditions.

Even though driven professionals crave feedback, they don’t always respond well to it, particularly when it’s negative.

6. Responding poorly to feedback. DeLong suggests that even though driven professionals crave feedback, they don’t always respond well to it, particularly when it’s negative. Dr. Larry Richard’s lawyer personality research shows that lawyers tend to be very low in resilience – defined in his studies, in part, as having a thin skin as far as critical feedback is concerned.³

7. Thinking you’re either highly successful or a major failure. When lawyers are unsuccessful, they can shift from feeling confident to feeling like a failure quickly. In addition, they can become hypercritical of themselves and just about anything (and anyone) else in their lives. This all-or-nothing style of thinking is an example of a thinking trap – an overly rigid pattern of thinking that can cause you to miss important information.⁴ To work your way out of this thinking trap, you need to identify the middle ground.⁵

8. Comparing. The large law firm where I worked had a practice of openly sharing attorneys’ billable-hour numbers. Each person’s hours were tallied monthly and reported to all other lawyers, names included. So, naturally, when the report was released, the first thing I did was compare myself to the other high producers in the firm. If I had a good month, then all was right in the world; if my hours happened to be lower than usual, then I thought I was a failure (see item 7 above).

9. Taking only safe risks. Lawyers must succeed at challenging tasks to get ahead, but their own mindset can prevent them from taking good risks because they don’t want to appear dumb or potentially fail. According to research by Dr. Carol Dweck and her colleagues, people with fixed mindsets think that ability (intelligence, for example) is fixed or static and therefore incapable of being developed beyond what already exists.⁶ This leads to a desire to look smart, avoid challenges when your smarts might be questioned, and give up easily.

10. Feeling guilty. Nearly every busy professional I know (especially working moms) feels guilty about something in his or her life. When busy professionals have too much on their plates, they are forced to pick some roles and tasks over others. The result is that other things get ignored, and this triggers that annoying little voice that says you are letting yourself or others down.

Conclusion

Sound familiar? Know that simple self-awareness goes a long way – if you can merely identify which traits get in your way, you can take the necessary steps to change your counterproductive behaviors into productive ones.

Endnotes

¹ Thomas J. DeLong, Flying Without a Net: Turn Fear of Change Into Fuel for Success (Boston, MA: Harvard Business Press, 2011).

² Learn more about Harvard Law School’s Executive Education program.

³ Larry Richard, Herding Cats: The Lawyer Personality Revealed, 7 LAWPRO Mag. 2-5 (2008).

⁴ Judith S. Beck, Cognitive Behavior Therapy: Basics and Beyond second ed. 181 (New York, NY: The Guilford Press, 2011).

⁵ Karen Reivich & Andrew Shatte, The Resilience Factor: 7 Keys to Finding Your Inner Strength and Overcoming Life’s Hurdles 121 (New York, NY: Broadway Books, 2002).

⁶ Carol S. Dweck, Mindset (New York, NY: Ballentine Books, 2006). See also David Scott Yeager & Carol S. Dweck, Mindsets That Promote Resilience: When Students Believe That Personal Characteristics Can Be Developed, 47(4) Educ. Psychol. 302-14 (2012).