Nathalia Benitez-Perez is the Director of the Mayor's Office of Civic Organizing for the City of Boston. She moved from Colombia to Spain to Boston, worked doubles at a restaurant while carrying a full course load at UMass Boston, organized campaigns across East Boston, and built programs like Block Parties, Spooky Streets, and Love Your Block — all with a team of three. In this episode, Nathalia sits down with Tom, Lorenzo, and Antonia to talk about what happens when the path that looks like falling behind actually leads somewhere meaningful. This one's for anyone who can't afford to separate the paycheck from the purpose.

TIMESTAMPS:
01:30 Colombia to Spain: Growing Up Between Countries
03:45 The 2008 Financial Crisis Changed Everything
05:50 Moving to the U.S.: New York, Florida, and Starting Over
08:10 Transferring to UMass Boston
12:00 The Brutal Schedule: Classes, Restaurant Doubles, and Two Days for Homework
14:30 "I Was Not Special at UMass Boston — It Was All of Us"
16:20 Why Unpaid Internships Were Impossible
18:03 Finding Purpose in Community Work
20:00 What Makes East Boston Special
22:15 Sunday Colombian Food Runs with Her Brother
24:00 Campaigns, Neighbors, and a Different Kind of Networking
25:00 "I've Always Been a Fixer" — Where That Instinct Comes From
27:30 Growing Up in a Household of Strong Women
30:00 Latina Identity, Hospitality, and Putting Others First
32:38 How Constant Moving Affected Friendships
35:00 Finding Home and Choosing to Stay in Eastie
38:00 "I Have Found My Community"
40:38 "I've Learned to Trust Myself More Than the Plan"
42:30 How to Join a Community: Talk to Your Neighbors
44:45 What the Office of Civic Organizing Actually Does
46:30 Block Parties, Spooky Streets, and Love Your Block
49:00 Law School Was Always the Plan — Until It Wasn't
51:00 Director at 25: "Pretending Not to Be Scared"
53:15 Why MBA, Not Law School: BU Questrom
55:00 Working for Mayor Wu as a Woman and Fellow Newcomer
59:00 "Instead of Forcing the River, Let the Current Carry You"
61:00 Advice for Anyone Who Feels Behind

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The office siren trend is all over TikTok — pencil skirts a little too short, one button undone, Bayonetta glasses, full femme fatale energy. It looks incredible on your For You page. But what happens when you actually wear it to work?

This week, we're joined by Stephanie Niles — NYC-born lawyer who's worked in investment banking, big law, and civil service — to break down the real gap between how TikTok influencers role-play corporate America and what actually flies in a real office.

TIMESTAMPS:

• 0:28 – Today's topic: the office siren trend & meet our guest Stephanie Niles
• 2:13 – OOTD: the crew shows off their fits (snake skin, real fur, and corduroy)
• 6:27 – So what actually is the office siren trend?
• 8:09 – TikTok influencers are role-playing corporate America — not living it
• 9:17 – Is return-to-office fueling the trend?
• 11:12 – Where did you learn how to dress for work? (Family, mentors & getting pulled aside)
• 13:30 – "It's like a dirty Halloween costume of someone playing work"
• 14:06 – Intent vs. impact: your outfit as a suit of armor, not a sword
• 18:10 – The jeans test: reading the room and office dress code politics
• 20:53 – Fashion as self-expression vs. conformity — and the double standard women face
• 22:22 – Accessories first: a safer way to show your personality at work
• 24:10 – Office fashion as a metaphor for work itself
• 25:37 – Do you plan outfits for the week? + shopping for your "work wardrobe"
• 29:07 – Word association: cleavage at work = "vulnerable"
• 30:00 – Is office siren actually empowering?
• 34:08 – Finding the balance: creativity without sexiness
• 35:05 – "If you're questioning the outfit, don't wear the outfit"

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Want to share your own career mess? Got an idea for an episode? social@realitygappod.com

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Note: We may earn revenue from some of the links we provide. The Reality Gap Pod is a production of Signal + Pattern LLC. Registered trademark.

#OfficeSiren #OfficeSirenTrend #WorkFashion #OfficeFashion #CorporateFashion #WhatToWearToWork #OOTD #WorkOOTD #CapsuleWardrobe #DressCode #TheRealityGapPod #RealityGap

What if the job you think is a dead end is actually your biggest career asset?

In this episode, Tom's cousin Pete joins the pod to talk about why grit beats polish, what he actually looks for when reviewing grad school applications (hint: it's not your GPA), and the real tradeoffs of taking the scenic route in your career. Plus, Lorenzo opens up about how getting DOGE'd has him rethinking his own path.

If you're stuck in a job that feels like it's going nowhere — this one's for you.

TIMESTAMPS

0:00 – Meet the "Better Barry" (and the Brady Bunch intro)

2:01 – Who is Pete? Woods Hole, Birkenstocks, and cracking gas

5:06 – Why geology? Field trips, fossils, and finding your thing

9:00 – Everyone went to grad school... except Pete

11:06 – The odd jobs era: valet, babysitting, and gas station hot dogs

13:00 – "Soul-crushing": what the field technician job actually looked like

15:41 – Day one: "Here's a broom, start sweeping"

17:18 – How hating your job becomes the best motivation

19:08 – The last-minute call that changed everything

22:15 – Plot twist: the dead-end job got him into Scripps

23:45 – What Pete looks for when reviewing MIT applications

26:48 – Reality Gap #2: Passion vs. building the "perfect" resume

29:42 – Antonia's passions: travel, food, and doing the dirty work

33:09 – Pete's brother, studying abroad, and 40 countries later

36:52 – Lorenzo reflects: what Pete's story means for his own path

39:28 – Getting DOGE'd and learning to see setbacks as opportunities

43:00 – 100 applications, 99 rejections: Pete's real journey to tenure

45:13 – The tradeoff no one talks about: starting a family at 40

48:00 – Pete's advice: why you should travel while you can

53:11 – Grit over polish: final thoughts

55:02 – Shameless plug for The Search + wrap-up

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Watch Or Listen On: Apple Podcasts | Spotify | YouTube

Want to share your own career mess? Got an idea for an episode? social@realitygappod.com

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Learn more at https://realitygappod.com

Note: We may earn revenue from some of the links we provide. The Reality Gap Pod is a production of Signal + Pattern LLC. Registered trademark.

#TheRealityGap #CareerAdvice #CareerChange #NonLinearCareer #Grit #GritOverPolish #JobSearch #CareerJourney #FindingYourPath #WHOI #MIT #AcademicJobs