Career reinvention and fighting for happiness across four professional chapters

Executive overview

Most people want to change their career or life but spend years paralysed by fear of judgment and failure. Liz Novello-Vaynerchuk moved through retail management, teaching, stay-at-home motherhood, and real estate — not smoothly, but reluctantly, with years of deliberation each time.

The throughline: every transition was driven by a refusal to stay unhappy, even when change felt impossible.

Fighting for your own happiness is a choice that requires action, not just desire — and it's always worth the discomfort.

Four career chapters and what drove each transition

• Left retail management after realising the job required mentorship she wasn't getting and skills she didn't yet have
• A discouraging professor steered her away from her planned teaching path; she pivoted to retail management for the money, then returned to teaching via grad school
• Taught first grade for six to seven years; won Teacher of the Year in only her second year — one of the first non-tenured teachers to receive the award in over 30 years
• Left teaching after having a child; extended maternity leave turned into eight years of full-time motherhood
• Entered real estate after five-plus years of talking about it — finally committing the day she overcame a fear of flying to board a flight with her brother

On fear, change, and the gap between wanting and doing

• Identified as someone who hates change, yet made more career changes than almost anyone in her family
• "Secret agent" first year in real estate: didn't tell friends and family she was an agent, for fear of failure and judgment
• Fear of mom-on-mom judgment — being seen as abandoning stay-at-home motherhood — was a major barrier to going back to work
• Talked about entering real estate for a minimum of five years before acting; the extended deliberation is the norm, not the exception
• The moment of commitment came from a small act of courage, not a grand plan

What stay-at-home motherhood revealed

• Postpartum depression was misunderstood at the time — perceived as either loving your baby or not; the reality was subtler: boredom and loss of identity, not rejection of motherhood
• The hardest part was the absence of hustle, interaction, and purpose outside the home
• Finding community — even one aligned friend at a parent-and-baby class — changed everything
• Motherhood reduced judgment of others: living through hard experiences creates empathy that sideline observation never does

Lessons from teaching applied to real estate

• Teaching 26 first-graders requires a tight schedule; that discipline translated directly into time-blocking as a real estate agent
• Taught self-esteem alongside curriculum — the goal was always more than content delivery
• Recognised she had no desire to become a principal; staying close to the work itself, not climbing, was the right call
• The same instinct — do the thing you're good at, not the thing that looks like advancement — applies in every field

On real estate: reality vs. expectation

• Early hype from social media growth (700 to 15,000 followers overnight) created external pressure that wasn't enjoyable
• Not "annihilating it" turned out to be freeing: business settled at exactly the pace and scale she wanted
• First real lesson: run with an opportunity when it comes, regardless of whether it feels like a leg up
• A good home at the right price sells in any market; negotiating room returning to the market is itself a signal of health
• Only sells homes she wants to sell, makes money she's proud of, works with clients she genuinely likes

On judgment, authority, and self-trust

• Trusted a professor's negative assessment of her teaching ability at 21 — a decision she now sees as misplaced deference to authority
• Motherhood taught her to trust her own knowledge of her children over expert defaults
• Judgment of others fills a void — people become less judgmental once they've lived through the experience they were judging
• The fear of being judged by other stay-at-home moms for going back to work is widespread; naming it reduces its power
• Accepting yourself — including what others see as flaws — is a process, not a moment; for her it solidified around age 40