The Messy Parts with Maryam Banikarim

Episode: Irina Novolselsky – Will I Ever Get a Job Again?

Release Date: August 4, 2025
Guest: Irina Novolselsky, CEO of Hootsuite

Episode Overview

In this candid, insightful conversation, Maryam Banikarim sits down with Irina Novolselsky, the CEO of Hootsuite, to unpack the real and often messy journey behind Irina’s “rocket ship” career. The episode centers on themes of relentlessness, resilience, and self-belief—especially during career pivots, periods of unemployment, and transitions into leadership. Irina brings vulnerability and humor to the discussion, reflecting on her immigrant upbringing, her pursuit of hard-won opportunities, and the emotional toll of navigating layoffs and high-pressure jobs.
Main Theme: The emotional and practical realities of navigating success—including failure, reinvention, and the discomfort of the “in-between” periods.

Key Discussion Points & Insights

1. The Emotions of Unemployment & Career Uncertainty

• Irina’s black hole experience: The existential anxiety of extended job searches and societal pressure.
  • “At some point, you’re out in this abyss of black hole of trying... you start getting these negative thoughts of, will I ever find a job? Am I just going to be unemployed for the rest of my life?” (Irina, 00:01)
  • The awkwardness and shame of answering “What do you do?” when between jobs.
  • How joblessness impacts personal identity and social interactions.
  • Turning point: Reframing unemployment as networking and opportunity—“I just turned it into a game and a hunt. It was like a puzzle that you were in the puzzle.” (Irina, 21:29)

2. Immigrant Upbringing & Relentlessness

• Family background: Fleeing Ukraine as refugees to NYC; Irina as an only child.
  • Parents re-starting life with nothing—“They never had a victim mentality.” (Irina, 05:19)
  • Building resilience and a “no plan B” mentality from scratch.
  • Early entrepreneurship: selling water and shoveling snow as a child; “I could buy my mom flowers for Mother's Day. I could get myself something. And it wasn’t even buying myself something... it was just knowing I could if I wanted to.” (Irina, 07:19)

3. Self-Financing and Education

• Working multiple jobs through NYU Stern:
  • “At $5 an hour, I wasn’t going to get there.” (Irina, 10:07)
  • Cold-emailing investment bankers, relentless pursuit of better opportunities.
  • On cold outreach: “You didn’t take it personally... no is not a personal statement to me.” (Irina, 13:38)

4. Career Transitions: Wall Street, Private Equity, and Fearless Pivots

• From Morgan Stanley to Apollo: Choosing hard work over party cultures; realizing passion matters more than prestige.
  • “I can’t win at this because I don’t love it as much.” (Irina, 17:35)
• Leaving without a job lined up: “I don’t know if it’s guts or stupid, to be honest...” (Irina, 19:29)
  • The emotional rollercoaster as months drag on.
  • “You start getting these negative thoughts... in the society we live in, the first thing they ask is your name, the second is ‘what do you do?’ When you’re unemployed you hear it really loud.” (Irina, 20:27)

5. Growth through Relentlessness and Grit

• Treating adversity as a puzzle: constant cold-calling, networking, looking for “chief of staff” or “business ops” roles.
  • “The thought of me not finding it was not an option in my brain.” (Irina, 21:29)
• Value in every job: “You don’t want to take a job where you know how to do 100% of it. That’s not fun.” (Irina, 22:12)
  • “A healthy amount is you should be able to give 60-70% of value to the business… but there should be a solid 30% you’re learning.” (Irina, 22:41)

6. Lessons in Authentic Leadership

• Early CEO experience: The trap of mimicking male or prior leadership styles—“I started implementing a lot of the things... and it was just a ton of bricks dropping.” (Irina, 27:19)
  • “He would never use exclamation marks in emails... for me, when I communicate, it was coming off cold. And I’m not naturally a cold person.” (Irina, 27:21)
  • Embracing emojis, authenticity, and her own leadership voice.
  • “You almost have double the job... doing the work and then editing, second-guessing yourself.” (Irina, 27:54)
• Three lessons for new leaders: (Irina, 28:23)
  1. Inventory your skills—What got you here may not take you further.
  2. Team investment—You can't "throw your body at things" as a leader of leaders, you must build the right team.
  3. Authenticity & boundaries—Set your own model for balance; prioritize wellness (vacation, sleep, exercise).

7. Finding the Right Fit: Waiting for the Trifecta

• Fifteen months of job searching between CareerBuilder and Hootsuite.
  • “One of the things I realized is time is your most precious investment. And I was willing to wait to find the right thing.” (Irina, 31:33)
  • Importance of industry undergoing change, a product that works, and a unique culture.

8. Social Media as Leadership Tool

• Initially fearful, coming from a background of privacy (“where my parents said their phones were tapped... not a natural thing”).
• Recognizing social as a key business channel: “If your customers are human, they’re on social media.” (Irina, 35:05)
• Pivoting from company-promotion to authentic content; balancing presence as an introverted CEO.

Notable Quotes & Memorable Moments

• On Relentlessness:
  • “You kind of just keep putting left foot in front of. And it probably wasn’t until the last five, ten years that people started attributing names to some of those traits... I don’t view myself as relentless. I just view that as forward.” (Irina, 02:55)
• On Seeking Opportunities:
  • “Sometimes naivety or just inexperience is one of the biggest gifts in life... you just did that because you don’t think.” (Irina, 13:20)
• On Not Taking Rejection Personally:
  • “People rejecting me, I don’t think is personal. People ignoring me, I don’t think it's personal. People saying no to me, it's just like, okay, you're just the wrong person, or, I’m asking the wrong person.” (Irina, 13:40)
• On Leadership:
  • “The things that make you successful to get to a certain point aren’t usually the things that'll make you successful at your next career moves.” (Irina, 26:32)
  • “As a leader, you kind of have to allow yourself the permission... What is it that you need to keep your energy and your machine running?” (Irina, 29:34)

Rapid Fire: Personal Side of Irina (35:48)

• Walk-on song: “I Will Survive.” (Irina, 35:52)
• Potluck food: "Olives. I know it's not actually food, but... they're really good." (Irina, 36:10)
• Alternative career path: Still building teams – “I've always wanted to build teams... I don't know what else I would be good at.” (Irina, 36:26)
• Reading lately: "Outlive" and multiple books at once; loves nonfiction and biographies (Irina, 37:00)
• Surprising fact: “I love sleep. I think sleep is the healthiest thing you can do. And I sleep at least eight hours... I will skip a meal to get sleep.” (Irina, 37:15)
• Views on ‘Balance’: “Balance for me—I set it for me... I feel a lot of gratitude to do what I do.” (Irina, 37:46)

Timestamps for Key Segments

• Unemployment & Self-Doubt: 00:01–01:12, 19:29–21:54, 30:56–32:31
• Immigrant Resilience: 02:37–07:38
• Early Entrepreneurship & Financing Education: 07:38–10:39
• Cold Emailing & Not Taking Rejection Personally: 10:39–13:50
• Private Equity to Zero: 16:24–20:15
• Lessons of Leadership Authenticity: 26:32–29:33
• Waiting for the Right Job: 30:56–32:31
• Social Media & Modern Leadership: 32:31–35:09
• Rapid Fire + Final Advice: 35:32–39:06

Parting Advice

• On action and self-belief:
  • “Whatever it is that you wanna do, just go do it.” (Irina, 38:49)
  • “Sometimes it’s scary, and the more you spend time on the scary, it just gets into your brain. So just one action, one step. Write the email. Take the phone call. Just do it.” (Irina, 38:55)

Tone & Takeaways

Both Maryam and Irina maintain a conversation that’s down-to-earth, honest, occasionally humorous, and deeply vulnerable. The episode serves as reassurance for anyone who feels lost, jobless, or pressured to “have it all together.” The recurring message: keep moving forward, embrace discomfort, ask for what you need, and remember you only need one yes.