We’ve Been Doing This Career Thing All Wrong

Bad advice. Ancient rules. Perfect interview answers. And other things we really need to stop believing.

By Chere B. Estrin

I’ve been in legal recruiting long enough to have heard approximately 14 billion pieces of career advice.

Some of it is excellent.

Some of it was excellent in 1996. Unfortunately, I remember it well.

And some of it needs to be taken outside, thanked for its service and quietly retired.

Yet every day, perfectly smart attorneys, paralegals, legal assistants and executives are still following career rules handed down from generation to generation like Grandma’s lasagna recipe.

Except the lasagna still works.

Here are a few career commandments we desperately need to stop treating as commandments.

“Never Leave a Job Before Two Years.”

Why?

What happens at 24 months? Does LinkedIn send you a certificate of completion?

If you made a terrible move, you made a terrible move.

The job wasn’t what they promised. The culture is dreadful. Your boss communicates primarily through clenched teeth. You’re doing nothing remotely resembling the position you accepted.

But you should stay another 14 months because somebody once told you it “looks bad” to leave?

No.

One short stint is explainable.

You accepted a job. It was wrong. You corrected it.

Seven short stints require a very good story.

There is a difference between making a career correction and establishing a migration pattern.

Know the difference.

“Don’t Make It About the Money.”

I love this one.

Employers make it about the money.

They have compensation committees, salary bands, bonus formulas, budgets, billable-hour requirements, realization rates, utilization reports and profitability meetings.

There are people in law firms whose entire job is figuring out the money.

There are people in law firms whose entire job is figuring out the money.

Then a candidate says she’d like $15,000 more and suddenly we’re concerned she’s “too focused on compensation.”

It’s a job.

They are paying you in money. Not gratitude. Not exposure. Not a lovely note from the managing partner saying, “You’re a rock star.” Money.

You are allowed to care how much.

Money shouldn’t be the only reason to take a job. Culture, opportunity, benefits, flexibility, commute, quality of work and who you’re working for matter enormously.

But let’s stop acting as though wanting to be paid market rate indicates a troubling character defect.

Try paying the firm’s Westlaw bill with “You’re a rock star” and let me know how that goes.

“Your Resume Should Be One Page.”

Please stop.

If you’ve been working for 18 years, I’d like to know what you’ve been doing.

You do not receive bonus points for reducing an entire legal career to something that fits on a cocktail napkin.

For an experienced legal professional, two pages is perfectly appropriate and generally plenty.

The answer isn’t to cut 15 years of relevant experience just to obey an ancient one-page rule.

Make the font smaller.

Not microscopic.

If I need a jeweler’s loupe to find your current position, we’ve gone too far.

The goal isn’t one page.

The goal is two strong pages someone actually wants to read.

And Now: The AI Resume

This is the newest career disaster.

Someone tells you:

“Just put the job description into AI and have it rewrite your résumé.”

Please don’t.

AI reads the posting.

AI reads your résumé.

AI sprinkles keywords everywhere.

Suddenly you are a “strategic, results-driven legal professional leveraging cross-functional synergies to deliver exceptional stakeholder outcomes.”

Yesterday you were Susan.

Today you sound like a consulting firm’s annual report.

Worse, candidates sometimes allow AI to reshape their experience so aggressively that the résumé starts describing the candidate the job wants rather than the candidate who actually exists.

Then comes the interview.

“So, tell me about your experience managing an enterprise-wide e-discovery migration.”

Susan:

“My what?”

AI is a tool.

Use it to improve clarity. Find buried accomplishments. Compare your résumé against a job description. Identify skills you genuinely have but forgot to emphasize. Clean up clunky language.

But don’t give AI a job posting and essentially say:

“Turn me into this.”

There is still one annoying step in the hiring process.

Eventually, you have to show up.

“Just Memorize the Interview Answers From the Book That Guarantees You’ll Get a Job in Three Days.”

You know the book.

Or the article.

Or the TikTok.

Or the career guru promising “The 10 Perfect Answers That Will Make Any Interviewer Hire You.”

Apparently, after decades in recruiting, I’ve been making this much too complicated.

“What’s your greatest weakness?”

“I’m a perfectionist.”

Where do you see yourself in five years?

“Growing with the firm.”

Why do you want this job?

“I’m looking for an exciting new challenge.”

Tell me about yourself.

“I’m a highly motivated team player.”

Congratulations.

You have successfully said absolutely nothing.

Then you leave thinking:

Nailed it.

No.

You conducted the conversational equivalent of beige.

Interviewers have heard these answers hundreds of times.

And now, thanks to AI, candidates can generate them even faster.

Interviewing isn’t a school exam where someone has hidden the correct answers in the back of the teacher’s edition.

Tell me about the impossible trial you helped pull together.

Tell me what happened when the partner handed you a disaster at 4:30.

Tell me how you found the error everyone else missed.

Tell me about the client you saved.

Tell me what you’re unusually good at.

Tell me something that makes the interviewer think, three candidates later:

“I liked her.”

You don’t ace an interview because you gave all the approved answers.

You ace it because they remember you after you’ve left.

“Don’t Apply Unless You Meet Every Requirement.”

This one stops terrific candidates before the employer ever gets the chance to meet them.

The posting asks for 10 years.

You have eight.

Apply.

It lists six software programs.

You know five.

Apply.

It asks for trial experience. You’ve helped prepare five major cases for trial, but only two actually reached the courtroom.

Apply.

It says AmLaw experience “preferred,” and you’ve spent your career at an excellent midsize firm.

Apply.

Notice a pattern?

I’m not suggesting that a first-year paralegal apply for General Counsel because she has “transferable skills.”

There is optimism, and then there is performance art.

But job descriptions are often wish lists.

“Required” sometimes means required.

“Preferred” means exactly what it says.

And occasionally the employer meets someone who has 80% of the list and 120% of what actually matters.

Let them decide.

Stop rejecting yourself before the employer gets the opportunity.

Recruiters already have people for that.

“Your Employer Will Notice Your Hard Work.”

Maybe.

Your employer may also be sitting in another office trying to remember your last name.

Hard work matters.

Invisible hard work is still invisible.

This doesn’t mean marching into the managing partner’s office every Thursday with a PowerPoint titled:

Why the Firm Would Collapse by Tuesday Without Me

Although I would probably attend that presentation.

It means knowing your value and making sure the people making decisions about your career know it too.

Keep track of accomplishments.

Did you improve a process?

Save money?

Take over responsibilities?

Train employees?

Handle a nightmare case?

Master new technology?

Increase efficiency?

Fix something everyone knew was broken but had apparently been promoted to “firm procedure”?

Write it down.

Performance-review season is not the time to stare at the ceiling thinking:

“I know I did something important in March.”

If you’re waiting for someone else to keep score on your career, don’t be surprised when they lose the scorecard.

“Don’t Burn Bridges.”

Generally, excellent advice.

But let’s stop pretending every bridge is the Golden Gate.

Some bridges lead directly back to places you spent years trying to escape.

Leave professionally.

Give notice.

Transfer your work properly.

Thank people who helped you.

Don’t send the 11-page resignation manifesto you’ve been secretly drafting since February.

And for heaven’s sake, don’t tell Bob what everyone has been calling him since 2019.

You don’t have to leave a job with scorched earth behind you.

But you also don’t have to maintain lifelong emotional custody of every professional relationship you’ve ever had.

Leave well.

Then move forward.

And My Personal Favorite: “Just Be Yourself.”

At an interview?

I don’t think so.

Be yourself at your professional best.

Your completely authentic self is wonderful.

Your completely authentic self may also eat cereal over the sink at 11:30 p.m. while watching a murder documentary.

The interviewer doesn’t need the entire package.

Authenticity doesn’t mean telling the interviewer every thought you’ve ever had.

It means sounding like a human being instead of a candidate assembled from LinkedIn buzzwords.

And Maybe the Biggest Career Rule That Needs to Die: “Play It Safe.”

Stay because you’ve already been there six years.

Don’t ask for the raise.

Don’t apply because you’re missing one qualification.

Don’t take the recruiter’s call.

Don’t explore something because you’re “not looking.”

Don’t leave because maybe next year will be different.

Careers aren’t built by recklessness.

But they aren’t built entirely by avoiding risk either.

Here’s an Estrinism:

You have to wake up in the morning and love it. Otherwise, don’t do it.

That doesn’t mean every day is wonderful.

It means you should occasionally look at your career and ask:

Would I choose this again today?

Not five years ago.

Today.

Career advice isn’t carved into stone tablets.

The workplace changed.

Hiring changed.

Technology changed.

Résumés changed.

Interviews changed.

You changed.

Some career advice remains excellent.

Some expired years ago, and nobody bothered to check the date.

And if someone insists that your 20-year legal career absolutely must fit on one page?

Smile.

Thank them for the advice.

Then ask them if they’d also like you to fax it.

Time to consider a change? Reach out. We’re here for you. 


Chere B. Estrin is the CEO of Estrin Legal Staffing and Estrin VIP. She is the President of the Organization of Legal Professionals (OLP), an online technology training company. Chere has written 14 books on legal careers, including Power Plays for Legal Professionals: Strategies to Move Your Career Forward; The Legal Professional’s Job Search Handbook, and Hot Flashes, Cool Resumes. Still Brilliant. Still Billable. Resumes for Legal Professional Women Who Aren’t Done Yet. (all available on Amazon.com). She can be reached at Chere@EstrinLegalStaffing.com

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