Law school, big law, lifestyle, AI, legal technology, small firm reality, student loan pressure and legal adjacent careers all collide in this conversation. Host Larry Port sits down with Jared Correia, who walks through his path from small liberal arts college English major and classics minor to Suffolk Law School, small firm practice, bar association work and founder of Red Cave Law Firm Consulting.

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Jared shares that he went to law school with no idea what he wanted to do, discovered he did not like practicing law, and pivoted into consulting after seeing how many firms lacked basic business management. Larry and Jared break down different practice areas, lifestyle practices like estate planning, the grind of personal injury and big law, why so many lawyers are depressed, and how AI and cloud software reshape research, document drafting and staffing. Listeners hear honest advice on knowing why you want to go to law school, understanding debt, exploring legal adjacent work and building skills in communication, sales, customer service and AI.

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Jared Correia is the Founder and CEO of Red Cave Law Firm Consulting, providing business management consulting services for lawyers and law firms, as well as technology and marketing consulting for legal institutions and legal-facing businesses. A former practicing attorney and bar association administrator, he has worked with thousands of law firms and hosts legal industry podcasts and events. Jared brings honest insight on law school decisions, small firm life, big law, legal technology, AI and alternative paths in the legal world.

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• Going to a small liberal arts college, choosing English and classics without a plan, joining the debate team and deciding to apply to law school late with a middling LSAT.
• How Jared chose Suffolk Law School over Santa Clara, went straight through without a break and then discovered through electives that he did not like any of the traditional profitable paths.
• Why he says he probably should not have gone to law school, and why students should understand what lawyers do, talk to lawyers, shadow, and avoid going in just for money.
• Clear examples of how different practice areas shape real life: personal injury as scratching lottery tickets and eating ramen, estate planning as a lifestyle practice with flexible hours, and the strain of litigation work.
• Honest talk on big law, billable culture, giving away your twenties, and why many lawyers feel trapped with significant student loan payments, old cars, no house and repetitive, stressful work.
• The emotional and mental load of lawyering: worst case scenario thinking, constant client crises, pessimism, and how that bleeds into personal life and fuels depression and burnout.
• Jared’s pivot story: leaving small firm practice, joining a bar association, moving into a consulting role for thousands of lawyers, using cloud software, social media and podcasting to build a profile in legal consulting.
• How AI and legal tech intersect with law firm work, why many lawyers are still not really using AI, what can be automated in document review and drafting, and why future lawyers should build strengths in sales, customer service and prompting AI.

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• Red Cave Law Firm Consulting
• St....

Anxiety is running high for new graduates and career changers as industries shift and the job market feels locked. Joseph Lewin joins Larry Port to talk about what’s behind the frustration so many students face as they send out hundreds of resumes without a response. They explore why traditional job applications fail, how to think about career direction, and what to do when your degree doesn’t lead to immediate opportunities.

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Larry shares his direct experiences mentoring college students and guiding his own kids through the career search process. The conversation moves from self-awareness and lifestyle choices to practical strategies for networking, exploring internships, and finding new ways to stand out in a crowded field.

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• Why so many recent graduates feel anxious about their job prospects
• How to figure out what kind of career actually fits your strengths and lifestyle
• The importance of honest self-assessment and knowing what you’re good at (and not)
• Real-world examples, like a real estate agent balancing flexibility with constant availability
• How the flood of computer science graduates changed the hiring landscape
• Where to look for opportunity in tech: DevOps, AI infrastructure, cybersecurity, and data analytics
• The value of networking and talking to people over mass resume submissions
• Why applicant tracking systems (ATS) have broken the job application proces
• How to reach out effectively on LinkedIn and what not to say when networking
• How internships act as extended interviews and lead to long-term roles
• The recurring theme: relationships drive career success at every stage

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• LinkedIn (for networking and outreach)
• DevOps and cloud infrastructure
• Cybersecurity and data analytics fields
• Applicant Tracking Systems (ATS)

Figuring out what career path to take is intimidating. Larry Port talks through the massive chasm after graduation, the luxury of choices, and the work of connecting who you are to the life you want. Joseph surfaces real tensions around hard skills versus the lifestyle you actually want, parental pressure, and the risk of walking a predetermined path. Larry shares personal shifts from photojournalism to software and entrepreneurship, why family dinner and coaching Little League mattered, and how looking at who you will become in a field can guide decisions.

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The conversation gets practical on the current AI transition, conflicting studies, what the tools can do right now, and why using them increases throughput. They compare startups and large companies, risk, culture, and wearing different hats, then map rising and retracting industries by paying attention to the news, demographics, energy, and the kinds of work that will be automated.

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• The massive chasm after college and why choices feel daunting
• Hard skills, aptitude, and whether the job translates to the life you want
• Parental pressure, predetermined paths, and the cost of avoiding uncertainty
• Looking at who you will be in a field by watching people ahead of you
• AI transition in October 2025, conflicting studies, and real use cases that increase throughput
• Startups versus large companies, culture, risk, and wearing different hats
• Entrepreneurship temperament, roller coaster moments, and time freedom
• Industries to watch: healthcare ecosystems, robotics, sales, energy, and roles supplying AI

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• ChatGPT
• OpenAI and Sam Altman
• Yale study; Stanford study
• Morgan Stanley
• Ernst and Young
• Goldman Sachs
• Robotics; humanoid robots
• DevOps

What should I do with my life? It is a question almost everyone has asked. Larry Port opens the conversation by exploring the difficult transition from school to the workforce and the overwhelming chasm that graduates face when trying to figure out what comes next. He reflects on the challenges of standing out with a degree that looks like everyone else’s while automation and AI reshape white collar jobs.

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Larry shares his own experience of discovering that photojournalism, though exciting on paper, conflicted with the family life he wanted. He highlights how overlooked careers, from user experience engineering to sales and finance, can be rewarding yet rarely appear on a college counselor’s radar. Alongside producer Joseph Lewin, the discussion focuses on listening to your inner voice, aligning career choices with personal goals, and paying attention to labor market trends. This episode sets the stage for a show dedicated to helping students, career changers, and professionals navigate the uncertainty of work and life.

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• The overwhelming transition from college to career and how to stand out
• Why a career on paper can look very different from real life
• Larry’s story of pursuing photojournalism and realizing its lifestyle trade-offs
• Careers that few people know exist, from user experience engineering to event planning
• How overlooked roles in sales and finance can align with personality and goals
• The importance of listening to your inner voice when making career decisions
• Paying attention to labor market news and societal trends to anticipate opportunities
• Why Dream Job Cafe exists and who will benefit from tuning in

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• Larry Port (Host)
• Joseph Lewin (Producer)
• Wall Street Journal (labor market trends mentioned)

Larry Port introduces Dream Job Cafe — a show about uncovering what careers are really like, beyond the glossy titles and résumés. Hear why this podcast exists, who it’s for, and how real conversations with professionals can help you figure out if a career path fits the life you want to live.