How to Ruin Your Career in 5 Easy Steps

Chere B. Estrin

As CEO of a prominent (yes, let’s acknowledge it here!), staffing organization, I talk to lots of unhappy or frustrated people, not exactly my favorite thing. As someone who loves coming to work, my Pollyanna attitude is that everyone should have the same experience. Sadly, that’s not the case. What I have found dealing with thousands of legal professionals throughout my career is that quite often, legal professionals blame the job they are in as the sole reason for unhappiness. As hard as it is to believe, many people do not recognize that their career has stalled. They blame frustration on the job they are in. It’s not necessarily the job, rather, how you are making choices about your career

A survey by VitalSmarts found that 83% of those surveyed had witnessed someone make a blunder that had catastrophic results for their career, reputation, or business, and 69% admitted that they themselves had done something that had damaged their careers:

  • 31% said it cost them a promotion, a raise, or even a job
  • 27% said it damaged a working relationship
  • 11% said it destroyed their reputation

It’s time to wake up and recognize that you may be experiencing these symptoms:

  • Unhappiness with the firm, usually management 
  • Routine and repetitious work translating to boredom
  • Lack of growth 
  • Below market salary
  • Overwhelming amount of work 
  • Consistently laid off
  • No upward movement (doing what you did 10 years ago)
  • Happy but like a puppy on a linoleum floor: lots of motion, going nowhere.

Let’s put it on the table: Here are steps you may have taken that are ruining your career:

  1. Taking a job that you know you won’t be good at. Sometimes people get so caught up in the quest to get a job offer that they forget to think critically about whether the job is one they’ll be good at. That shortsightedness can lead to doing things like trying to hide key weaknesses, bluffing about your knowledge, or trying to sell yourself for a role despite reservations from the hiring manager. The danger here is that if it works, you’ll have vastly increased the chances that you’ll end up in a job where you struggle or even get fired. Muddling through is not a good option because that can have long-term effects on your reputation. Colleagues and managers who knew you in that job will think of you as mediocre (which is not what you want for future jobs). Plus, there’s an cost of opportunity spending time in a job that you’re not great at when you could have been spending that time building an excellent reputation somewhere else. Results? Inability to get a new job when the cat is out of the bag.
  2. You lack a sense of purpose. Purpose is a belief that your life matters and that you make a difference. It is a sense of being guided by meaningful values and goals. You will be most engaged in your work when the mission and goals of the organization also matter to you—and when you feel you can contribute to the bigger picture. We all want to build castles, not just lay bricks. When you have purpose, you experience:
  • Increased optimism, resiliency, and hope
  • Joy, happiness, and satisfaction experiences more often
  • Better physical health with a lower risk of death
  • Being a more engaged employee
  • Feeling a greater sense of belonging at the firm
  • Increased career satisfaction
  • Being a leader in the workplace
  • Higher income

Are you aware of your sense of purpose? For example: you may be in a position assisting in corporate transactions. However, deep down inside, you would rather do something that is more community oriented, despite the probable lower pay. You may be in a large firm where you are a small cog in the wheel and cannot discern exactly what purpose you play other than putting more money in the shareholders’ pockets. That is not purpose and does not necessarily give you a sense of pride in your work. 

According to Forbes,  you should strive to pursue a job or career that offers opportunity. Pursue work that is meaningful, intellectually challenging and spiritually rewarding. Find a job that enables you to help others, promotes positive change and serves a higher purpose. You want to ensure that your work is aligned with your core values and principles and could possibly make the world a better place.  I understand that these are lofty, aspirational goals. It is rare to find work that offers a sense of purpose. In fact, it’s more likely that your job won’t offer intrinsic, meaningful rewards. You may enjoy the fact that your job is associated with a social status that people find impressive or that it helps you earn a nice living, but somehow, you still feel that something is missing. Can you sum up your purpose in one sentence? I, for example, say, “My purpose is to find people their dream jobs and when I do, I feel incredible career satisfaction that I have help make someone happy.”

If you feel that there is a lack of purpose in your career, you can choose to make a change. 

  1. You have stayed much too long at one job. There’s a bias these days against employees who stay much too long at one job. In past years, when your parents or grandparents were in the job force, they were rewarded with a gold watch and an office party as they retired from one job after being there umpteen years. Today, employers want to see that you have changed jobs. Why? If you haven’t, they think you show no ambition. If you stay in a job simply because it offers long-term security and you can do your work with your eyes closed, the best years of your career might slip by. This lack of ambition could come back to haunt you later when you’re getting passed over for promotion and struggling to improve your earnings and workplace status. This always amused me because if there is anything that employers hate most of all, it’s someone who hops around. 

Staying too long doesn’t only hurt you with your current employer; it makes new employers shy away. 

While some staying power is attractive to an employer, they don’t want to invest in a new employee only to have them leave in a year or two. That’s considered job hopping.  Many employers see the risk and cost of prying away a long-term employee as too great. They wonder if the person can adapt and how much drive and motivation they have. 

Here are the cons of staying in one place too long:

  • You end up knowing only the systems your firm has in place. When you go to another firm, you may not have the expertise you need. For example, there are legal professionals, particularly litigation paralegals, who have little eDiscovery experience. They don’t know the most popular software programs. They set out to get a new job and discover their options are extremely limited. Few employers today will hire without those skills. Can you say, “not very marketable”?
  • Your skills may become too niche and you are pigeonholed. 
  • You can be viewed as “part of the furniture”. The reality of becoming “too comfortable” at a firm is that powers that be don’t really see your skills and importance. They assume that you will always be there. Like the desk or the wall, you’re part of the landscape. This can cause your compensation and potential career path to fall behind the market as your employer pays more attention to newer employees. Frequently, you are passed over for promotions. 
  • New and current employers alike wonder if you can adapt and how much drive and motivation you have. 
  • You make less money as over the years, you typically receive a cost-of-living increase but never a huge jump as you might if you change jobs. 

When you stay in the same job, or at the same level, for too long, you will get typecast. This damages your career success because it gets harder for people to envision you in a different position or at a senior level. If your goal is to be in management, don’t overstay your role as an individual contributor. If your goal is to be a supervisor, apply for jobs that provide that responsibility earlier rather than later in your career. If you are the assistant but want to be the team leader, get your game plan together and work it. Do what it is that you need to do. Trust me, your firm is not going to do it for you. 

There are some pros to staying in one place: consistency, larger bonuses, internal advancement, and gaining expertise. It’s a good rule of thumb to consider the 7-10-year mark as a critical point in decision making as to whether you’re a “lifer” at your current firm. For some folks, being a “lifer” is just fine, however, it is important to consider the career limiting aspects of this decision. Just remember, if you are not an attorney, the chances of becoming a partner are not going to happen. (I hope this is not the first you are hearing this……) On the other hand, if you are an attorney and shooting for partnership track, most tracks today are 6-7 years and staying put may be the right thing to do.

  1. Assuming good work will be recognized. This is huge. Most employees think, “If I do a good job, the firm will notice, and I will get great raises or promoted.” Guess what? The firm hires you to do a good job. That’s what you are expected to do. If you’re a hard worker, it’s easy to just assume all your efforts are getting noticed by management, without bragging about your successes. However, in many instances, your manager won’t even notice what you’ve done or that you’ve gone the extra mile in your work. All the while your less-than-competent colleagues have risen through the ranks because they were able to point out their contributions to the firm’s overall success. I know it’s hard to brag. However, there are ways to do this without seeming pretentious. It’s absolutely imperative you get the word out about your successes. (That’s a whole other article.) 

In a similar vein, don’t assume there is an established ‘pecking order’ within your firm and an orderly queue for promotion. Firms want to keep their best people onboard and motivated and this means allowing talented professionals to rise through the ranks. If you’re seen as someone who has leadership potential, you may be able to secure a promotion before your natural turn. Ways to achieve this include volunteering for extra responsibilities, exceeding billable hours, leading a team, finding a way to increase efficiencies and boosting revenue. However, if you are a paralegal in a firm without avenues to move up the ladder, it may be time to go. 

  1. No career goals. Frequently, when I give seminars or interview candidates, I will ask, “What are your career goals?” Most of the time, they will tell me what they don’t want. (I don’t want to work overtime; I don’t want to work for a large firm; etc.) But they cannot articulate what they do want. That’s because they haven’t set any career goals. In fact, the majority of legal professionals do not have career goals. They are of the opinion that the firm will notice them and do something about their career. Not happening for you? I am not surprised. The old trite and meaningless, “What will you be doing in five years?” can rarely be answered. Is this you? Are you letting your career drive you rather than driving your career? Hmmmm……probably. This would be akin to taking a bow and arrow and aiming for that round target with the red circle in the middle. Just as you go to pull the bow and arrow, someone removes the target. Then what?

Additionally, if you want to move forward, you are going to have to map out a route to get to your destination. What goals are you going to achieve and by when? Do you want to be a team leader but are now just part of the team? What do you have to do to meet that goal? Believe me, no one is just going to pick you out of the crowd. Do you need to take a course? Get cross-trained in a different specialty? Give up your remote position and go onsite? Plan, plan, plan. And, if you are a person of “a certain age”, start asking yourself, “How do I want to go out?” Reality, folks. Reality. 

At the end of the day, no one is going to look out for your success better than you, and if you don’t do it, it won’t get done. Don’t ever presume that you will eventually be rewarded. There are far too many people calling me because they are unhappy and they think it’s the job, not the choices they have made. Frequent searching for “the next thing” is not the best strategy. Once every two years is probably a good cadence for checking what your next challenge should be, inside or outside your current firm. Most people think that all it takes to destroy one’s career is a huge mistake. But sometimes even the small mistakes can pile up and before you know it, you’re the miserable and calling me……(not that I don’t want to hear from you!)

Chere Estrin is the CEO of Estrin Legal Staffing, a top nationwide staffing organization with a five-star Google Business Review rating.  She has been a well-known name in the field for over 20 years. She was recently interviewed by The Wall Street Journal and Fortune Magazine ( and was named “One of the Top Women Leaders in Los Angeles” She has written 10 books on legal careers, hundreds of articles and has been written up in publications such as the Los Angeles Times, Chicago Trib, Newsweek, Entrepreneur and others. She received the prestigious Los Angeles/Century City Women of Achievement Award and was a finalist for the Inc. Magazine Entrepreneur of the Year award. Chere is a founder of the well-known nationwide Paralegal SuperConferences and a co-founding member of IPMA (International Practice Management Association).. She gives numerous webinars including those for Lawline and LawPractice. She is a former administrator at an AmLaw 200 firm and Sr. Vice President in a $5 billion company. Reach out at: or visit her website at

2 Replies to “How to Ruin Your Career in 5 Easy Steps”

  1. This is a fantastic article!! Why aren’t more people talking about this when it comes to career planning?

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