161: The BEST Career Advice From 25 Years As A Lawyer You'll Ever Hear | Jason Stuart Weiss

There’s often a gap between what school teaches and what real life demands. Jason Weiss found that to be true for becoming a lawyer. Now, after 25 years in the legal world, he shares the practical, hard-earned lessons that apply to anyone trying to succeed in a high-pressure, people-driven profession.

Whether you’re a lawyer, leader, or someone simply figuring out how to show up fully in your work, this episode is a masterclass in resilience, communication, and redefining success on your own terms.

In this episode, you’ll learn:

• Why “the practice of law” never really ends
• How to recover from losses and develop thicker skin
• What not to do when giving or receiving professional advice
• How to pick clients (and when to walk away)
• Why communication and follow-up might be your most valuable assets
• The surprising ways AI and legal tech can (and can’t) help
• When to rethink your entire career and how to do it responsibly

Timestamps:

00:16 – Jason’s post-law school “welcome to reality” moment

01:38 – First win in court and the difference real-world law makes

02:57 – Why law is a “practice” (and not an exact science)

03:58 – How a judge’s mood can influence your case

04:20 – Jason’s book: The Sht They Never Taught You in Law School*

05:54 – Universal skills: follow-up, integrity, and knowing your values

08:52 – Law school theory vs. real-world advocacy

11:25 – What happens when you lose and have to face the client

13:46 – Learning who not to work with as a lawyer (and business owner)

15:59 – The $60K mistake Jason made with a client—and what he learned

19:06 – Common misconceptions non-lawyers have about lawyers

21:25 – The power of saying “I don’t know”—and circling back

24:43 – Clients today expect instant clarity: managing modern expectations

25:55 – Thick skin, self-care, and knowing when not to take it personally

28:06 – Continuous learning, CLEs, and the role of AI in law

30:49 – Batman’s utility belt: how Jason views AI as a legal tool

33:43 – Worst professional advice Jason ever received

36:29 – Honesty, mistakes, and always having a plan of action

37:07 – Advice for those considering law school

38:35 – Why some lawyers are miserable—and how coaching can help

42:26 – What coaching is (and isn’t) supposed to do

44:23 – Finding motivation 25 years into the legal grind

45:35 – Why showing up is more powerful than talent

47:02 – You don’t have to respond instantly—just communicate well

47:46 – What Jason has doubled down on since writing his book

49:24 – Final advice for aspiring or struggling lawyers

50:14 – Where to find Jason online

About Jason:

Jason S. Weiss is a litigator who handles all aspects of business and commercial litigation. He has dealt with matters involving breach of contract, tortious interference with business relationships, title, property, non-compete clauses, commercial and residential landlord tenant matters, elder abuse, partnership disputes, trade secrets, RICO claims, fraud, real estate litigation, consumer protection, American’s with Disabilities litigation, tenant/landlord matters, medical marijuana litigation, personal injury and other various business related lawsuits.

He was recently appointed as a Board Member of Benefits Specialist Inc. and voted President of Leadership Coral Springs Class of 2011. Jason is also a former adjunct professor of Sports Law at Nova Southeastern School of Law, a former adjunct professor of the graduate level course Sports Law at St. Thomas University and a former judge for the Broward County Teen Court Program.

Jason has extensive sports and entertainment law experience, including representing...