Challenges for Jobseekers in Mid-Life and Beyond

Last week, I was interviewed on the very awesome “Chris and Amy Show” on KMOX-FM in St. Louis. Chris and Amy are a very up-tempo couple so we took a jocular approach to a serious topic: the difficulties of finding a new job after age 40 and whether it’s ever too late to make a career change.

The short answer is yes, it’s more difficult to find a job when you’re 40+, but no, it is never too late to change careers (unless you think it is!).

To be successful in either endeavor, you must have a deep understanding of how the career game works and what you bring to the table that will make you valuable to an employer, regardless of your age or past experience.

At Career Strategies Group, we specialize in job searching and career changes for professionals in mid-life, which I define as age 40 and older. My oldest clients are in their 60s and 70s, and they’re not looking for part-time retirement jobs — they’re seeking real, full-time, intellectually challenging and fulfilling employment.

Re-imaging Your Job Search

Winning a new job in your 40s and beyond means being creative in your job search. You can’t rely on what I call the “Traditional Triad” of job search methods: classifieds, recruiters, and old-fashioned networking. These methods are much less effective for the mid-life jobseeker than they are for their younger colleagues.

Your job search itself has to reflect the value you bring to a new employer. If you see yourself as a creative problem-solver, you need to prove it by conducting a creative job search. Get smart about innovative versus traditional job search methods — it is much different today than it was the last time you looked for a job! (For information, click here: https://www.careerstrategiesgroup.com/job-search-services/tactics/ )

Understanding Your Value

A key to a successful job search is understanding what you’re good at, and that means looking beyond the obvious, your practice area expertise. We had a client in his late 50s who ran a very successful niche practice for 18 years. When his major corporate client moved on, his business started to fail, and he came to me for career coaching.

My client kept insisting he was “just a lawyer,” and given the narrowness of his niche practice, he felt defeated before he even started. It took a lot of work, but I finally helped him realize he was, in fact, a skilled businessman. He had created his firm from nothing and grew it to a respectable size. He handled IT, HR, training, employee relations, client service, advertising, marketing, purchasing, accounts payable/receivable, sales, and more. What made him successful for all those years wasn’t just his legal skills — it was all these other attributes. When he finally understood this, he was able to get a high-paying job in operations management in an entirely different field.

There are lots of examples like this:
• The bankruptcy lawyer who became a documentary film producer.
• The elderly small-firm associate who became a construction project manager.
• The late-middle-aged personal injury attorney who turned his hobby of managing his stock portfolio into a $400k job in wealth management.
The list goes on and on.

Practical Tips for the 40+ Jobseeker
While there is much more to it, here are some practical tips that can help you in your 40+ job search:

• Remove Graduation Dates: If you graduated more than 20 years ago, remove your class years from your resume and LinkedIn profile. There’s no need to advertise your age!

• Show Only Recent Job History: Just show your job history for the last 20 years. You can add earlier positions, but only if they’re relevant, and they should be in an encapsulated format.

• When the Interviewer is Younger than You: If you are being interviewed by someone much younger than you—a very common occurrence for my clients –don’t bore them with your old war stories. You need to understand their current problems, needs, and potential opportunities. Focus your discussion on these areas and how you can help with them. Approach the interview as an informed problem-solver, not a jobseeker.

• Sell Your Future, Not Your Past: Employers are buying your future, not your past. If an employer thinks you can solve their problems, they won’t care how old you are or where you went to school. Know their issues and what specific skills and perspectives you bring that will enable you to deal with those issues successfully.

One parting thought: The average age for a Fortune 500 CEO is 57.7 years. There are CEOs in their 60s, 70s, 80s, and even 90s. You are not too old to reach new career heights!

To hear my interview with Chris and Amy, click here: https://www.audacy.com/kmox/hosts/the-chris-and-amy-show-on-kmox

If you are an attorney or senior executive and you’ve been thinking about exploring your career options or discovering “what else is out there” for you, or if you are not sure how to even start a job transition process, get in touch with me today for a virtual cup of coffee. You will receive a confidential, no-cost consultation to discuss your situation and goals, and will also get expert advice on how to launch your job campaign.

If you would like to receive the “Beyond the Bar” newsletter every 2 weeks, make sure to hit subscribe to stay up to date. If you have any questions about your career, click here

Talk is Cheap. It’s Results that Count.

We give a lot of advice in this bi-weekly missive about how to conduct an effective job search and how to get out of your own way and find a high-paying career that you actually enjoy. But talk is cheap. Does what I teach, preach and impart to clients really work?

Yes, it does. (You expectedme to say that, didn’t you?)

The truth is I am researching how Artificial Intelligence is impacting job search and hiring. I had planned to write about that this week, but I am still neck deep in research. Since I am not ready to write about AI and needed a topic for today’s newsletter, I started looking on my PC for potential topics. Fortunately, I stumbled across these Career Strategies stories and comments from clients.

I am happy to share them with you now.

* Using what he learned from our program, at our insistence a client reached out to a former law firm colleague he didn’t like, didn’t get along with, and had said bad things about when they worked together. The former colleague was actually glad to hear from our fellow! Several weeks later, the colleague called and said he had a client who was looking for someone with our man’s experience. The hiring company did a series of interviews with our client, including flying him overseas to meet with their Board. Our client walked away with a post as US General Counsel at a compensation package nearly six times what he had been earning in a law firm practice!

* Our client was interested in transitioning from litigation to Professional Development. There was a major annual Professional Development conference in Washington, D.C. that we felt could have been a bonanza for our client, but the conference was very expensive. We looked at the numbers with our client, did our ROI estimate, and recommended they spend the bucks.

I then did some networking for my client and called a “graduate” of mine who had transitioned from law firm attorney to professional development executive years before. (BTW, “graduate is a term I use for my clients who successfully obtain new positions. Most of my clients become “graduates.”) Not only did my former client say he would be happy to help my current client, he said he was a featured speakerat the event and in fact, had obtained his first professional development job years prior by following our advice and going to the conference, when he met people that led him directly to a career change.

* This isn’t a success story per se, but attests to the power of what we teach. Our client said he learned that we were right: “If you are going to tell them you can solve their problems, you damn well better know what their problems are before you say you can solve them. What I learned from you is that you have to do your homework before interviewing with a company.”

This seems self-evident, but there’s more to it than meets the eye. When I am putting a marketing campaign together for a client, it is very detailed and thorough. It contains action items, talking points and much more. When clients use a line like “I can help solve your problems,” I make them prove it. I put them through what I call “the interview from hell,” and make them support their claims. I will do this with a client multiple times until they come up with answers that will impress a senior business leader. I will not accept slovenly intellectual thinking, nor will the decision-makers who hire my clients. Part of what we bring to the dance here is that I have run businesses or corporate business units for many years, and understand what it takes to be successful.

* This last client is not a graduate yet – as of today – but has two firm offers and one we feel will be coming in within the next few days. Getting three offers sounds great, but it can be very hard to pick the best one. We help with that very critical process by providing objective, non-emotional evaluation of the options. Here’s part of what my about-to-be graduate told me:

Fiest, I want to thank you. The “cold call” e-mail I sent to the GC/VP of (Company Name Deleted) didn’t initially yield anything until…he called me out of the blue.  He said he saw my communication (a pitch letter and resume we had written for my client) and wanted to know what I wanted. So I told him! We had a good dialogue, but there were no openings.  Then he called this month and said that is about to change. They have decided to go through a reorganization.

Second, you were right.  They don’t advertise these positions.  You have to get on the radar before that.  Your method works – even for lawyers!

Third, I just had my first-round interview with the GC/VP.  I think it went quite well.  He is reorganizing the legal department in 3 weeks, after which the interview process will continue.  He explained he is not the sole decision maker. I will interview with other VPs (marketing, sales, etc.).  He said I should be prepared to speak with non-lawyers from (Location Deleted), who are very smart businesspeople but have no patience for legalese. I told him – who does, other than other lawyers?

“Anyway, I wanted to express my gratitude. Whether or not I land this gig, I am grateful.”

[Editor’s Note: This is the offer that is pending, but the other two offers are in hand.]

Please note that these are actual cases of people who have worked with me. I am not creative enough to make up stuff like this. If I were, I’d be in Hollywood writing screenplays! Nah, not really. I have found my niche and love what I do. I can help you feel the same way.

If you are an attorney and you’ve been thinking about exploring your career options and/or discovering “what else is out there” for you, feel free to contact me. If you are not sure how to even start the job search process, then by all means get in touch with me today for a virtual cup of coffee. You will receive a confidential, no-cost consultation to discuss your situation and goals, and will also get some expert advice on launching your job campaign.

If you would like to continue receiving Beyond the Bar Newsletter every 2 weeks, make sure to hit subscribe to stay up to date. If you have any questions about your career, click here

What It Means to Enjoy Your Job: The Mid-Life Lawyers’ and Executives’ Guide to Job Satisfaction

While some people doubt it, it is possible to enjoy your job. I mean really enjoy your job. I am not here to sprinkle fairy dust and sing kumbaya about finding joy in the your job everyday. Lawyers and executives who have been around long enough to know that “living the dream” usually involves more complex problem-solving than it does sipping margaritas on a beach.

But the truth is that it is possible to enjoy your job and make very good money.

Let’s dive into what enjoying your job really means.

The Value of Liking What You Do.

Liking your job doesn’t mean you have to love every single minute of it. I love my job but there are some days I’d rather phone in sick. Liking your job is about finding those moments that make you feel good about what you are doing. It’s the sense that, at the end of the day, you did something worthwhile and meaningful. It’s a feeling that you are not wasting your intellect and talents on things that don’t matter to you.

The Mid-Life Crisis Cop-Out.

It’s no coincidence that many lawyers and executives start thinking about exploring their options when they hit their 40s. Ah, “ye olde mid-life crisis,” that tumultuous time when some decide the answer to their problems is to buy a Porsche or Bimmer. But here’s a radical thought: instead of blowing your money on a European sports sedan, why not invest in finding joy in your job? Mid-life should be less about superficial thrills and more about finding real, sustainable satisfaction in your work.

Finding Your Niche.

Enjoying your job starts with finding your niche. For lawyers, it might mean spotting issues, doing research, training younger associates, negotiating great deals. What are the parts of your job that you really like and at which you excel? For executives, it may be the sweet spot where your strategic vision clicks into place and you then lead your team toward producing great results. It’s these pockets of time where everything just flows, and you feel good about your day. Identify those elements in your work! What’s your niche?

There are good careers out there that are based on the things you like to do and do well, and which deliver a feeling of accomplishment and meaningfulness.

Work-Life Balance: Not Just a Myth.

Work-life balance is not a unicorn — it exists! But achieving a good balance requires effort and boundaries. Enjoying your job means making sure it doesn’t consume your life. It’s about having the courage to close the laptop and actually leave the office (physically or metaphorically) at a reasonable hour. It’s about making time for the things that matter outside of work – family, hobbies, wives, husbands, golf – you know, the things in life that are important to you. The only ones who will remember how many hours you worked each week are your loved ones … the very people that you didn’t spend enough time with.

The Satisfaction of Mastery – a Two-Edge Sword.

There’s a joy in being good at what you do. For mid-life lawyers and executives, this often means leveraging your years of experience to navigate complex challenges with relative ease. It’s the satisfaction of seeing a project through from inception to completion, knowing that you have nailed it. Mastery is something that can make you feel good, but if the mastery you have doesn’t bring career satisfaction – if the results of your mastery aren’t fulfilling to you — then you need to apply it in a way that does. Identify the areas where you feel you have mastery, then look at other career areas where that skill set is valued.

The Importance of Mentorship.

One often overlooked source of job satisfaction is mentoring others. There’s something incredibly rewarding about sharing your hard-earned wisdom with those just starting out, or who are having problems grasping a legal concept. Watching them grow and succeed because of your guidance can give you a whole new perspective on your career. If helping the professional development of others is important to you, then that skill can be the foundation for a new career.

Conclusion: Joy in the Journey.

So, what does it mean to enjoy your job? It’s about finding those elements that make you feel that what you are doing really matters. It’s about applying your talents toward results that you feel are worthwhile. Most of all, it’s about having time to enjoy your family and your loved ones, and to have a life that is more than your job. For experienced lawyers and executives, it’s not about chasing a fantasy; it’s about embracing the reality of a career well-lived and finding joy in the journey.

If you are an attorney and you’ve been thinking about exploring your career options and or discovering “what else is out there” for you, but are not sure how to even start the process, get in touch with our team today for a virtual cup of coffee. You will receive a confidential, no-cost consultation to discuss your situation and goals, and will also get expert advice on how to launch your job campaign.

If you would like to continue receiving Beyond the Bar Newsletter every 2 weeks, make sure to hit subscribe to stay up to date. If you have any questions about your career, click here

How to Prepare for an Uncertain Job Future

Fear of job loss today is running rampant in the legal profession. The impact of the Trump economic program, the draconian cuts in the civil service and of course, the potential impact of the tariffs, are  causing businesses (including law firms) to take stock of where their businesses are heading and make adjustment accordingly.

Believe it or not, we are also seeing job cuts, especially for younger lawyers, because of Artificial Intelligence – yes, good old technology has advanced enough already that law firms in the US and overseas are turning to AI instead of 1st and 2nd year associates. We’ll have more on this in upcoming editions. Now back to the issue at hand.

I have been writing quite a bit lately on dealing with a real or potential job loss in terms of techniques to employ. This time I want to look at how to prepare yourself emotionally.

Before you allow your mind to race out of control trying to take in all the various options, this simple list of 6 reminders will help keep you on the right path.  Implementing all, or even some, of these pointers, is sure to be helpful.

1) FIND A MENTOR OR COACH.

This sounds self-serving (because it is!), but in fact this is good advice. Don’t be afraid to ask for help. There is no shame in consulting with a coach to overcome the hurdles standing in the way of your job search success.

An experienced coach can fill in many of the knowledge gaps that their clients have about “what’s out there” and how to make a transition. Reading self-help books and blogs are fine as supplements, but reading alone is not a substitute for getting mentored by people who know the ropes.

2. GET PREPARED.

Lawyers conduct research and fact-finding every day. Use that skill when getting ready for a job search or career change. Knowing you are prepared is the best way to fend off  feelings of futility and doubt. Start by taking an inventory of your skills — not just your practice area skills, but the ones that make you good at what you do.

Also, start getting smart about the world of work. Research job functions. Talk to people about their jobs. Contact trade and professional associations involved in fields in which you may be interested. You may find you are qualified for many more positions than you think!

3. DON’T YIELD TO YOUR FEARS.

Lawyers are not risk-takers by nature, and they like to be on solid ground before they put forth opinions. They tend to come up with reasons why they cannot do something that, in fact, they can do. In this job market, a defeatist or overly cautious attitude can doom a job search and career.

If, while contemplating your next career, you get excited about a certain job category, go for it! Don’t yield to a lawyers’ knee-jerk fear of the unknown. We have helped lawyers transition into entertainment, broadcasting, the arts, public affairs, motivational speaking, sports marketing, entrepreneurship, and many other areas that seemed crazy or impossible.

4. BE A GOOD LISTENER.

Ask people to share their stories. If you meet someone who has a job in which you may be interested, ask them how they got there. You can learn a great deal from the experiences of others. Connect with people! The more you can relate to and learn from others, the more confident you will become in your ability to make a transition.

5. GET RID OF BACK-UP PLANS.

Beware of the “doom and gloom” mindset. Focusing on a worst-case scenario will undermine your career development aspirations. One of my favorite quotations, from Henry Ford, is: “If you think you can do something, you are right. If you think you cannot do something, you are also right.”

I am not a pie-in-the-sky type, but I definitely believe that if you think you are going to fail at a task, you will fail, but if you think you will succeed, you will succeed. Focus on making a plan for your success. Avoid back-up plans because they divert your energy. Don’t be sending our resumes for jobs you don’t really want “just in case.” Try to push worry to the side and replace it with positive thinking! You can do this!

6. LOSE YOUR ANGER.

You only get one shot at this life. If you are filled with anger that you have lost your job for no valid reason, you are looking backwards, and that makes it difficult to move ahead. Give yourself a few days to be bitter and to grieve, but then switch gears, start looking forward, and take action. Any action in your job search, no matter how small, is better than no action at all.

If you are an attorney and you’ve been thinking about exploring your career options and or discovering “what else is out there” for you, but are not sure how to even start the process, get in touch with our team today for a virtual cup of coffee. You will receive a confidential, no-cost consultation to discuss your situation and goals, and will also get expert advice on how to launch your job campaign.

If you would like to continue receiving Beyond the Bar Newsletter every 2 weeks, make sure to hit subscribe to stay up to date. If you have any questions about your career, click here

Determining Your Next Career Move: A Guide for Attorneys and Executives Over 40

Yesterday I spoke with my elder daughter, Lindsay, about her career. She just turned 41 and is having a career re-evaluation. She is right on time: Consistently over the years, the most common age for people to first reach out to Career Strategies for help is, you guessed it, 41.

My daughter has been a UX designer (something to do with websites) and an account executive for a tech company for the last 7 or so years. Before that, she did marketing communications and brochure production for a financial services firm. In college, she made money as an event photographer and as a waitress. She is also an orchestral-quality string bass player and a fine pianist.  She is a talented young woman with very diverse skills.

The tech company recently laid off my daughter and most of its staff. She’s not sure what she wants to do with her career. She could easily get another UX job, but she’d gotten bored and become generally unfulfilled by the work. She is ready for a change, but not sure to what!

Sound familiar?

Like my daughter, you have solved complex problems for your clients. But roteness and boredom may have set in, especially because you have mastered your practice area and for the rest of your life, you know it will be the same thing over and over and over.  Making this realization brings about a period of reflection and the question: “What’s next?”

Lindsay asked me if I could help her figure out her possible career options. I understand the transferrable skills of lawyers and executives, and can help them identify the realistic new career possibilities, but I’m not real swift when it comes to viable career alternatives for techies or musicians.  The best I can do for her is to offer general advice.

You may find this advice helpful, too.

1. Reflect on Your Achievements

Start by listing your career accomplishments. Consider the cases you’ve won, the deals you’ve closed, the projects you’ve led, and the results you have produced for your clients or companies. Don’t take these things for granted. You are solving problems every day at work. Start by listing them.

2. Identify Your Core Skills then Divide Them into Likes and Dislikes

What makes you good at what you do? It’s not your experience – it is the skills you have developed while gaining that experience! Make a list of your skills. Include both hard skills (such as specific legal expertise, negotiation, strategic planning) and soft skills (such as leadership, communication, problem-solving). Next, divide the skills into two columns – skills you enjoy using more and skills you enjoy using less. What skills are you most passionate about? Write them down.

3. Analyze Your Work Preferences

What aspects of your work do you find most fulfilling. Do you enjoy client interactions, courtroom appearances, strategic decision-making, or mentoring junior staff? Conversely, consider the tasks that you find less interesting. Perhaps it’s research or hunting for clients or dealing with personnel issues. Looking at your work function preferences will help you determine the type of work you want to focus on next.

4. Assess Your Values and Motivations

What drives you in your career. Is it the pursuit of justice, financial success, intellectual challenge, or making a positive impact? What makes you feel good about what you do? Understanding your core values and motivations will guide you towards career options that align with your personal principles. What would provide a sense of fulfillment and meaningfulness in your next job? Start making a list.

5. Evaluate Your Work/Life Balance

What do you want for work-life balance? At this stage in your life, you will have different priorities than you did when you first got out of law school or college. Back then, putting in 70 hours per week at the firm wasn’t such a big deal, but when you are 40+ you may want to spend more time with your family and be able to get to your kids’ soccer games and school plays. You may want to have more time to pursue your personal interests. This is an opportunity to ensure your next career aligns with your priorities. I have worked with numerous 40+ attorneys who want to exchange their 2,400 billable hours so they can spend time with their families … or start one!

6. Dare to Explore New Opportunities

Don’t be afraid to explore new opportunities within and outside your current field. Attend industry conferences, trade shows, networking events, and seminars to learn about emerging trends and potential career paths. My lawyer clients have transitioned into legal and non-legal positions in broadcasting, sports, auto racing, Wall Street, academia, motion pictures, fashion and more. They didn’t have experience in these fields, but they brought intellectual agility, issue-spotting, problem-solving, negotiation and many other skills that made them valuable … and employable.

7. Don’t believe in the Myths

There are many myths about career change for professionals. A big one is that you have to go back to the bottom career rung again. Another is that you will make less money. A third is that you can’t compete against people who have experience in the industry or job function that you don’t have. Bull. I say again: Bull. I have been navigating major career transitions for lawyers and senior executives for several decades, and I know these are just myths. You can go in at a high level, make as much money or more than you have been making, and can triumph over candidates with more experience on point than you. Those are facts.

8. Be Prepared. Study and Learn What you Need to Know. Fake the Rest.

At one point in my career, the TV and home video production company that I was with (and to this day still love) was sold to a VC and dismantled. I was out of a job. But, using a create-a-job technique that I now teach my clients, I coaxed an interview with a computer technology company.  I did not know a file server from a process server, but before the interview I learned everything I could about the company, its products, its competitors and its people. When I went in for the interview, I knew almost as much about the company as they did. I got the job, and later became an inside member of its Board. I have a friend, in his early 60s, whose company failed during Covid. He’s a liberal arts – analytical kind of guy, not a techie, but he saw an opportunity in a nearby company in another industry that was looking for an analytical type. The job required knowledge of Sequel, a very complex data integration program that does SQL inquiries. (I have no idea what that means). So in his 60s, he took on the challenge of learning Sequel and he got the job over people who knew the program cold. Why? Because he brought other skills to the table that the techies didn’t.

9. Embrace Change and Stay Positive

Finally, embrace the change with a positive mindset. I work with clients who are looking to make positive changes in their lives. They are nervous, skeptical and scared, but they want more out of their lives. Career transitions can be daunting, but they also present opportunities for growth, reinvention and reinvigoration. Stay open to new experiences and be willing to step out of your comfort zone. Remember, it’s never too late to find where you belong.

If you are an attorneyor senior executive and you’ve been thinking about exploring your career options or discovering “what else is out there” for you, or if you are not sure how to even start that process, get in touch with me today for a virtual cup of coffee. You will receive a confidential, no-cost consultation to discuss your situation and goals, and will also get expert advice on how to launch your job campaign.

If you would like to continue receiving Beyond the Bar Newsletter every 2 weeks, make sure to hit subscribe to stay up to date. If you have any questions about your career, click here