Adulting101 Masterclass: Career, Money and Life Skills School Failed To Teach

You avoid the hard conversation. You skip the networking event. You stay quiet in the meeting because you are scared of sounding dumb.

In this episode of Adulting101 Masterclass, host Heather Redisch explains how to get comfortable being uncomfortable and why confidence never shows up before the hard moment. It shows up because of it.

Heather tells the story of a Gen Z professional at an HSBC fireside chat who admitted she avoids mistakes at all costs because she cannot stand the feelings that take over after she makes one. That instinct could be the very thing holding her career back. Heather also opens up about forcing herself to attend workout classes alone across New York City, walking in with no plan beyond finding a spot at the back.

This one gets into why discomfort leads to growth, practical networking tips for recent college graduates, and how to move past the fear of making mistakes so you can actually learn from them. Heather breaks down how to network after graduation on LinkedIn without it feeling forced, and why a text message can never do what a face-to-face conversation with a friend or manager can.

If you are working on building confidence in your 20s, or you already know you should get comfortable being uncomfortable but keep finding reasons to avoid it, this one is for you.

Episode Breakdown:

00:00 Why Getting Comfortable Being Uncomfortable Matters

01:45 Introducing Heather's Core Coaching Philosophy

04:01 The HSBC Fireside Chat And Fear Of Mistakes

06:27 Why Your Network Is Your Career

08:55 Overthinking LinkedIn Requests And Imposter Syndrome

11:14 Speaking Up And Saying Yes To Meetings

13:37 Walking Into Yoga Classes Alone In New York

15:58 Dating, Leagues, And Building Human Connection

18:27 Choosing A Hard Conversation Over A Text

Connect with Heather Redisch:

Visit the Adulting101 Masterclass website

Follow Adulting101 Masterclass on Instagram

Grab your free post-grad checklist! 

Podcast production and show notes provided by HiveCast.fm

You walked out of the interview feeling great. Then three days pass and you have no idea when to follow up or what to say. That silence is the hardest part of any job hunt, and it is exactly what Marissa Klein and Jamie Sztoser help their clients push through every day.

Marissa and Jamie are sisters and co-founders of the dreamcatchers™, a career strategy and job search firm built on more than twenty years of combined recruiting experience. On this episode of Adulting101 Masterclass, host Heather Redisch sits down with them to share job search tips for recent grads who keep applying and keep hearing nothing back.

They break down how to follow up after a job interview without feeling like you are bothering anyone, and why so many job opportunities are filled before you ever see them posted publicly. Marissa explains why this generation is overconnected yet under-networked. Jamie shares how to network for your first job when reaching out to a stranger feels unbearable, plus practical career advice for young professionals still figuring out what a dream job even means. They also cover a job search strategy for Gen Z and how to use LinkedIn to find a job instead of scrolling past it.

Press play for job search tips for recent grads that go beyond the resume, and to learn why the human on the other side of the process matters more than any algorithm.

Episode Breakdown:

00:00 Welcome And Meeting Marissa And Jamie

02:08 How Heather, Marissa, And Jamie Connected

04:58 Why Competitors Should Collaborate Not Compete

09:39 Why Gen Z Is Overconnected Yet Under Networked

16:55 Building The Dreamcatchers™ From A Family Staffing Firm

26:30 The Dream Catcher Method Explained Step By Step

28:07 Finding The Dream Job Versus Finding The Dream In The Job

31:16 Why Job Search Feels So Emotional For Everyone

44:07 How Long It Really Takes To Feel Settled In A New Job

50:02 The Follow Up Strategy Most Job Seekers Skip

55:08 How To Network Your Way Past The Applicant Tracking System

1:00:35 Turning Discomfort Into A Communication Skill

1:03:34 Closing Advice On Getting Your Foot In The Door

Connect with Marissa Klein and Jamie Sztoser :

Visit the dreamcatchers™ website

Follow the dreamcatchers™ on Instagram 

Follow the dreamcatchers™ on Tiktok

Connect with Heather Redisch:

Visit the Adulting101 Masterclass website

Follow Adulting101 Masterclass on Instagram

Podcast production and show notes provided by HiveCast.fm

Moving to a new city with no friends is hard enough. Figuring out how to make friends as an adult in a new city, without networking events or forced small talk, can feel impossible.

Nate Hiser wasn't sure where his idea would lead. After years of ski resorts, backpacking through Latin America, and a stint in Australia, he landed in Chicago and posted on Instagram inviting strangers to dinner. He expected seven replies. Over 600 people applied to join.

On this episode of Adulting101 Masterclass, host Heather Redisch sits down with Nate Hiser, founder of 1000 Chicagoans, to unpack how one small idea turned into a citywide waiting list. Nate walks through the moment his phone blew up and his nervous system could not keep up, plus why he keeps the dinners small instead of chasing bigger crowds.

The two talk about making friends after college, why loneliness in your twenties is more common than most people admit, and how to build community in a new city without it feeling forced or transactional. Nate shares the mindset shift behind it all: getting comfortable being uncomfortable, and doing the thing before you feel ready.

If you have wondered how to make friends as an adult in a new city, or simply how to meet new people as an adult without a script, this episode hands you a real starting point. Press play to hear how one dinner invite turned into a movement, and what Nate wishes someone had told him before he started.

Episode Breakdown:

00:00 The Dinner Invite That Sparked 1000 Chicagoans

02:26 From Ski Resorts to Corporate Sales

04:43 Working Remotely for Seventeen Months in Latin America

09:13 Choosing Chicago After Years Abroad

14:13 How to Make Friends as an Adult in a New City: The First Post

17:48 The Night His Phone Would Not Stop

20:13 Capping the Guest List to Protect Real Connection

26:52 What People Actually Talk About at Dinner

30:34 Time Blocking, Brick, and Running a Side Project

36:11 Advice for His Twenty-Two-Year-Old Self

Connect with Nate Hiser:

Follow 1000 Chicagoans on Instagram

Subscribe to 1000 Chicagoans 

Visit the Adulting101 Masterclass website

Follow Adulting101 Masterclass on Instagram

Podcast production and show notes provided by HiveCast.fm

Getting the job was the easy part. The moment you accept the offer, the rules change, and nobody hands you a manual for them. On this episode of Adulting101 Masterclass, host Heather Redisch breaks down the unwritten rules of the workplace that decide who earns trust, who gets the best opportunities, and who people want on their team.

Heather explains why watching your new environment matters more than trying to fix it right away. She shares the exact phrase she uses to ask a question instead of sounding critical, and why that one shift changes how people see you in a room. She also gets specific about meetings: when to arrive, when to put your phone away, and what your video background is quietly telling people.

You'll hear why reliability is the skill nobody talks about but every manager notices, plus the simple habit that builds trust right after a meeting ends. Heather walks through how to manage up at work, including a personal user's manual you can build to explain how you work best.

This episode covers workplace communication tips for new employees, workplace etiquette for your first job, how to build trust with your manager, and how to make a good impression at a new job. If you're starting a new job or managing someone who is, this conversation lays out the unwritten rules of the workplace so you don't have to learn them the hard way.

Episode Breakdown:

00:00 Intro: the unwritten rules of the workplace

01:07 Why culture fit beats early opinions

03:35 Swapping criticism for curiosity with coworkers

05:47 Showing up prepared and present in meetings

10:39 Taking notes and staying off your laptop

15:28 Sending recap emails that build trust

17:43 Choosing Slack, email, or a call

22:37 Solving problems before running to your manager

25:04 Managing up and your personal user's manual

29:55 Why reliability is the real career skill

Connect with Heather Redisch:

Visit the Adulting101 Masterclass website

Follow Adulting101 Masterclass on Instagram

Podcast production and show notes provided by HiveCast.fm

A great answer to "tell me about yourself" can't save you if you already lost the interview in the lobby. On this episode of Adulting101 Masterclass, host Heather Redisch breaks down the unwritten rules of job interviews and how to make a good first impression. Many of these expectations are never formally explained, yet they can shape how a candidate is perceived long before the interview really gets underway.

Drawing on more than 25 years of recruiting experience, Heather shares what hiring managers and recruiters notice before, during, and after an interview. She explains how to research a company before an interview beyond a quick scroll through the website, why the message on your voicemail could quietly cost you a callback, and why the way you treat the receptionist can carry more weight than your answers.

Once you are in the room, that same attention to detail carries into your body language. Mirroring your interviewer's posture can shift the energy in the room, and a limp handshake tells someone about your confidence before you say a word. Heather also talks about the questions candidates can use to evaluate the company in return. Asking about onboarding, feedback, and how a company actually lives its core values can reveal a lot about what working there may feel like. She closes with her take on the thank-you note after a job interview, including why a thoughtful follow-up can matter and why a generic AI-written note may not be worth sending.

This episode is full of interview tips for recent college graduates and anyone relearning the unwritten rules of job interviews for a new job market. If you have an interview coming up, this is a useful reminder that the small details can matter just as much as the answers you prepare.

Episode Breakdown:

00:00 Why the unwritten rules of job interviews exist

02:22 Generational gaps in workplace communication norms

04:42 How to research a company before an interview

09:23 Your voicemail and email response habits matter

11:45 Arriving early and reading the room correctly

16:11 Why reception and elevator etiquette get evaluated

18:59 How to make a good first impression fast

23:22 Interview body language tips and mirroring the room

25:42 Smart questions that reveal a company's real culture

30:28 Thank you note after job interview and biggest mistakes

Connect with Heather Redisch:

Visit the Adulting101 Masterclass website

Follow Adulting101 on Instagram

Podcast production and show notes provided by HiveCast.fm

You can't budget your way to financial independence if you're too scared to ask for a raise or send a DM.

Host Heather Redisch sits down with Ella Katz, content creator and founder of Taller Toddlers, to talk about how to become financially independent in your 20s after leaving a stable job at ABC News.

Ella reflects on the year she spent working with Heather and the money habits she built along the way, including the ritual she built just to check her bank account without panic. She gets honest about financial independence from parents, the guilt that came with early support, and how she is learning to spend on her own terms instead of copying what she grew up watching.

Ella also opens up about quitting her job to freelance before the income caught up. She talks about learning how to negotiate a higher salary even when her hands were shaking, and about practicing networking without fear of rejection well enough to land guests like a Dancing with the Stars pro.

Press play to hear how to become financially independent in your 20s from a former Adulting101 student who is still figuring it out.

Episode Breakdown:

00:00 Meet Ella Katz Of Taller Toddlers

02:11 Leaving ABC News For Something More

08:21 Rethinking The Word Influencer Online

12:49 What Taller Toddlers Is All About

16:43 Biggest Surprises Of Your Twenties

20:56 Building Confidence To Network Without Fear

26:36 Talking Openly About Money And Guilt

33:59 Building A Weekly Money Ritual

37:56 Freelancing, Boundaries, And Avoiding Burnout

43:57 Rapid Fire Questions With Ella

Connect with Ella Katz:

Follow Taller Toddlers on Instagram

Subscribe to Taller Toddlers on YouTube

Follow Taller Toddlers on Tiktok

Connect with Heather Redisch:

Visit the Adulting101 Masterclass website

Follow Adulting101 on Instagram

Podcast production and show notes provided by HiveCast.fm

Nobody hands you a manual for life after college. One day you have a schedule, a campus, and your best friends down the hall. The next day you are expected to build a career, a routine, and a whole new identity on your own. This episode gives you the playbook.

On Adulting101 Masterclass, host Heather Redisch sits down with content creator Love Always Annika. Known as the online big sister to nearly a quarter million followers, Annika is two years into her own post-grad transition and landed her job offer. She secured a job offer in October of her senior year, months before most of her classmates even started applying. She shares the networking moves that helped her get an early start.

Annika breaks down the red blazer trick recruiters never forgot, the one motto she gives every student she coaches on job hunting, and the surprising reason a structured workweek made her feel calmer than college ever did. She also gets honest about maintaining friendships after college when your closest friends scatter across the country, and why she spent five months resetting before her first day of work.

If adjusting to adulthood after college feels overwhelming, this conversation offers practical advice from someone a few steps ahead. Her guidance applies whether you graduated last month or still feel stuck two years later. Press play and start building a life after college that you love.

Episode Breakdown:

00:00 Meet Annika, the Online Big Sister for Life After College

01:18 What Graduation Day Feels Like

04:25 Long-Distance Friendships and Intentional Post-Grad Relationships

07:00 Why a 9 to 5 Routine Feels Better Than College

11:30 Taking Five Months Off Before Your First Job

13:18 Why Campus Recruiting Beats Online Applications

15:00 The Job Search Formula That Lands Interviews

19:56 How to Stand Out at Career Fairs and Networking Calls

25:22 Why Your Twenties Are Harder Than Anyone Admits

27:50 Setting Goals You Control and Ignoring Social Media Pressure

30:06 Stop Overthinking and Trust Simple Mental Health Resets

33:45 Building a Personal Brand While Working Full Time

Connect with Love Always Annika:

Follow Love Always Annika on Instagram

Follow Love Always Annika on TikTok

Connect with Heather Redisch:

Visit the Adulting101 Masterclass website

Follow Adulting101 Masterclass on Instagram

Podcast production and show notes provided by HiveCast.fm

You know that feeling of watching everyone around you hit their milestones while you're still figuring out how to make rent? That's a quarter-life crisis after college, and it's exactly what Heather Redisch walks through in the first episode of Adulting101 Masterclass. She opens up about her first job in New York, a boss who taught her more about resilience than patience, and the moment she realized her closest friends were getting promoted and falling in love while she felt stuck at the starting line.

Heather also gets into the life skills school doesn't teach, from reading a paycheck to negotiating a raise to spotting a red flag boss before it's too late. She traces her path from a psych major with no plan to a recruiter navigating the aftermath of September 11 in Manhattan, and eventually to building her own coaching practice around one idea. Adulthood should come with a guide.

Along the way, Heather explains how reading The Anxious Generation shaped her thinking on why Gen Z lacks confidence in interviews, and how growing up on smartphones changed the way an entire generation learned to communicate. If you're working on how to build confidence in your 20s or just adjusting to adulthood after graduation, this one hits close to home.

Press play and hear how Heather Redisch turned her own quarter-life crisis after college into the blueprint for Adulting101 Masterclass, the show helping young adults feel a little less alone in figuring it all out.

Episode Breakdown:

00:00 Welcome to Adulting101 Masterclass

02:05 Choosing New York over grad school

06:53 Landing a job in four days

09:15 A $32,000 salary and a brutal boss

13:56 Leaving that job to start over

18:27 September 11th and the move to Chicago

23:11 Coaching grads through a confidence gap

27:31 The Anxious Generation and the smartphone effect

32:11 Feeling stuck at the starting line

34:33 Building the business in one weekend

Connect with Heather Redisch:

Visit the Adulting101 Masterclass Website

Follow Adulting101 Masterclass on Instagram

Podcast production and show notes provided by HiveCast.fm

Adulting101 Masterclass is the life skills podcast for young adults navigating the real world — and for the parents who want to see them succeed in life and managers who want to help them thrive in business.

Because the real world doesn’t come with a manual.

No theory.

Adulting101 covers: