Episode Overview

Episode Title: Giving you fresh starts, career crossroads, and hustle guilt
Hosts: Alex and Jon
Date: January 13, 2026
Podcast: Give It To Me Straight by Dear Media
Theme:
This episode blends unfiltered relationship anecdotes, honest reflections on parenting, and straight-talk advice about life's crossroads – including career pivots, navigating family boundaries, and overcoming hustle guilt. Alex and Jon draw from their own lives as new parents and entrepreneurs, answering listener questions with their signature candor and humor.

Key Discussion Points and Insights

1. Entering the New Year: Parenting, Vacation, and New Normals

• New Year Mindset & Parenting Realities
  • Alex and Jon reflect on the slow adjustment into the new year, especially as first-time parents.
  • They discuss the difference between taking a vacation before and after having a kid—debating the merits of bringing their daughter, Lucy, on trips and the realities of “vacationing” with a young child.
    • Notable Quote:
      • “Take your kids on vacation and at least they're crying somewhere warm.” – Alex (02:22)
  • Humorous storytelling about taking Lucy to Vegas, their struggles with child travel, and the sheer quantity of “stuff” needed for even a night away.
• Advice for New Parents:
  • Expect travel and trips to feel entirely different post-kids; be strategic, align on expectations, and don’t romanticize what’s fundamentally “work in new locations.”

2. Family Dynamics, Holidays, and Navigating Parenthood

• Holiday Recaps: Chaos and Nostalgia

  • Funny and heartfelt moments from Christmas and New Year’s, including Jon’s dad assuming the role of “Santa” for Lucy, and the family chaos recorded for posterity.
    • Notable Moment:
      • The "Santa/Pepe" confusion—Jon's dad repeatedly forgetting his role, causing both frustration and laughter (04:32-05:18).

• Family Trips and Their Limits:

  • A one-hour drive for New Year's proved surprisingly intense due to the logistics of traveling with kids.
  • Couples often have clashing perspectives on family trips—Alex values memory-making while Jon focuses on logistics and stress.
  • Candidly address the struggle to balance fun, rest, and not feeling guilty for feeling overwhelmed or unhappy during "special" events.

3. Raw Reflections on Their Marriage After Kids

• Real-Time Relationship Check-In

  • Openly discuss their increased arguments, fatigue, and the challenge of liking each other in this “season” of parenting.
    • Notable Quote:
      • “On a scale of 1 to 10, how much do you think we like each other in this season?” – Alex (08:21)
      • Jon notes: “We are battling a little bit more lately…we're just both mentally tired.” (08:40)
  • Frustration with unsolicited advice (especially about sleep), and how comparison only makes the struggle harder.

• Parental Guilt and Outsider Judgement

  • Both hosts express anger at the societal expectation that hardship is always to be silently endured, especially after trauma or loss.
    • Notable Quotes:
      • “Two things can be true at once…we wanted this, [but] we're never allowed to complain.” – Alex (10:34)
      • “If you think that, drink bleach.” – Alex (10:18, 11:32)

4. Adjusting to New Parent Life: Work-Life Balance

• Milestones and Seeking Help
  • Lucy’s developmental milestones (rolling over!), and the next phases of parenting—considering extra help (nanny, family).
  • The anxiety of bringing a stranger into the home versus relying on family.
• Physical & Emotional Impacts:
  • Parenting’s effect on routines: Jon talks about how having a baby has even disrupted his pooping schedule—humorous, but all too real.
  • Sleep deprivation, changing habits, and conversations about health tech (like the Oura ring).

5. Social Media, Algorithms & Modern Life

• Algorithm Woes
  • Jon’s TikTok/Instagram feeds now filled with disturbing and bizarre videos based on one-time viewership; the couple riff on how algorithms shape what you see and even how you feel.
    • “Your algorithm is kind of like my dreams.” – Alex (22:30)
• Childhood Memories & Social Anxiety
  • Alex shares an anecdote about a childhood bike accident that shaped her perceptions and social anxieties, including comparisons to her sister.

6. Listener Q&A — Fresh Starts & Career Crossroads

[Q&A starts at 37:01]

Hustle Guilt and Productivity (37:01–41:35)

• Listeners ask how Alex and Jon cope with decreased productivity since having Lucy. Both share their struggles with “productivity addiction” and redefining self-worth.
  • “Not looking at taking care of Lucy as being productive hurts.” – Jon (39:00)
  • They admit they’re still working on shifting their mindset and invite listener strategies.

Financial Struggles with a New Baby (43:00–45:30)

• Sacrifice is inevitable if you want to build wealth and a family, especially if you start from a less secure position. The hosts urge listeners to get creative, accept it will be hard, and take pride in smart sacrifices.

Mid-Life Career Change Fears (45:29–48:34)

• Confidence and impostor syndrome are tackled—Alex encourages being “shameless” like her young hustler self, reaching out for what you want. Jon admits it’s hard for some people to even identify their strengths/interests and suggests enlisting friends’ help for perspective.

Stay-at-Home Mom Seeking Remote Work (48:35–51:22)

• Practical suggestions: virtual assistant, online tutoring, managing content or emails for small businesses. Jon also jokes about starting a home daycare for someone who misses having more kids—“best of both worlds.”

Career Change Requiring Family Sacrifice (51:23–53:20)

• Weighing the opportunity cost of a career shift that would mean long absences from home, Alex emphasizes that ultimately, mutual spousal agreement is key; regret for missed opportunities can last a lifetime.

Marriage, Trust, and Deal-Breakers (53:21–58:10)

• One listener describes discovering her husband’s major gambling problem. Both hosts are blunt: this is a severe breach of trust, not what “bad times” in marriage means.
  • “Vows don’t include lying. He broke your vows.” – Alex (54:32)
  • “When you break those vows, these are grounds to be done.” – Alex (55:05)
  • Jon, especially, says plainly: “You know the answer. Everyone’s better off [without him].” (57:18)

Starting a Business vs. Staying Secure (58:29–62:22)

• Entrepreneurship is about more work, not less, but for the right person, it’s more rewarding. Both caution the listener: “Owning a business doesn’t mean more time, just more flexibility.”
• Advice: If you’re going to regret not trying, you have to try.

Family Boundaries, Burnout, and Moving Cities (62:33–69:47)

• In-depth issue: one listener feels crushed under the weight of extended family needs and friend/family drama.
  • Alex: “A move doesn’t fix your problems; boundaries do.” (66:10)
  • Jon is more optimistic about distance helping: “If your husband can’t do it on his own, you do it for him by moving.” (67:10)
  • Both agree: mastering “no” as a sentence is essential.

Fun, Lighthearted Qs

• Dating the boss’s son in secret: Jon, tongue-in-cheek—“Stick with it! Marry up!” (70:38)
• Life hacks and recommendations: keep it simple. (black coffee at Starbucks, minimize decision-making).

Notable Quotes & Memorable Moments

• On Parenting and Marriage:
  • “On a scale of 1 to 10, how much do you, like, think that we like each other in this season?” – Alex (08:21)
  • “We are battling a little bit more lately…we're both just mentally tired.” – Jon (08:40)
• On Social Criticism:
  • “Two things can be true at once…we wanted this, [but] we're never allowed to complain.” – Alex (10:34)
  • “If you think that, drink bleach.” – Alex (10:18, repeated humorously throughout follow-up conversation)
• On Productivity After Kids:
  • “Not looking at taking care of Lucy as being productive hurts.” – Jon (39:00)
• On Relationship Dealbreakers:
  • “Vows don’t include lying your vows. Like you. He broke your vows.” – Alex (54:32)
  • “I'm supposed to just forgive that because we're married? That doesn't give you a pass to do whatever you want.” – Alex (55:02)
• On Cringe and Hustle:
  • “I cringe at that, but I'm also very proud of who I was then because I had no shame.” – Alex (30:12)
• On Family Boundaries:
  • “No is a sentence.” – Alex (70:09)

Timestamps for Major Segments

• 02:22 – Parenting “vacation” debate; travel with babies
• 04:32 – The Santa/Pepe family call story
• 08:21 – Relationship check-in: how much do we like each other in this season?
• 10:18 – “Drink bleach” as a retort to rude social commenters; discussion about parenthood complaints
• 15:04 – Lucy’s milestones and the dilemma of outside help
• 20:09 – Jon’s struggle with sleep, health, and the Y (YMCA) crowd
• 21:23 – Social media algorithm “hellscape”
• 37:01 – Listener Q&A begins
• 39:00 – Productivity guilt with a new baby
• 43:21 – Getting out of financial holes post-baby
• 45:29 – Career change fears in your 30s
• 48:35 – Remote work for a stay-at-home mom
• 51:23 – Career leap requiring family separation
• 53:21 – Husband’s addiction – when is it grounds for divorce?
• 58:29 – Risking a stable job for entrepreneurship
• 62:33 – Burnout, boundaries, and whether a move will fix family issues
• 70:28 – Secret relationship with the boss’s son
• 71:03 – Life hack: just get black coffee
• 73:44 – Final wrap-up and recommendations

Tone and Dynamic

The conversation is raw, self-deprecating, and honest—as always. Alex and Jon riff, tease, and occasionally argue lightheartedly, while still addressing the vulnerable realities of marriage, parenting, work and personal growth. Their advice is grounded, a bit irreverent, and always direct, with plenty of laughter offsetting the heavier topics.

Conclusion

This episode brings practical, no-BS advice for anyone navigating new chapters—be it in parenting, career, or relationships. With a blend of comic relief and sincerity, Alex and Jon remind listeners that growth is uncomfortable but necessary, and that self-compassion (and a sense of humor) are as valuable as any practical strategy.