Why Stamps of Approval Matter in your Career Path: Strategic Career Moves with Erin Lydon

Erin Lydon is an experienced C-suite leader and advisor with expertise across multiple startups and industries. She’s also a frequent speaker on workplace equity, closing the gender wage and financial gaps, and organizational leadership. Most recently, Erin was President of Poker Power, an EdTech company with a mission to teach one million women how to play the game of poker and the game of life.

This article will be helpful for professionals aiming to understand the importance of strategic career moves and relationship-building, and anyone wanting to understand the benefits of building credibility and taking calculated risks.

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There's a part of me that, given the chance, would choose to structure my career the same way Erin Lydon did.

When we spoke, Erin had the same excitement about startups that I had during my first venture, with a twinkle in her eye and an untainted love for the messiness of it all. The difference between us, however, was our timing. I was in my late 20s when I quit my corporate job to launch my first startup, while Erin had an impressive tenure of high-profile positions before diving into the startup world.

I couldn't help but think it would have been nice to experience my startup journey without the financial worries I had at the time. At 26 I went all-in on my first business, cashing in my savings to cover startup costs and then my investments a year later to support myself. Erin, on the other hand, built her professional foundation like a pyramid, allowing her to reach the top in a planned way.

Erin's career path offers valuable lessons for structuring one's career: making strategic moves, being honest about wanting to earn a lot of money, taking calculated risks, and understanding the importance of building relationships with influential people from the beginning. Erin now gets to enjoy the excitement of startups with financial security in place.

While there is no right or wrong way to build a career, it is a smart strategy to acquire power, influence, and wealth early on, then use the latter part to take larger risks and pursue unconventional paths.

Exposure to Power and Influence

Being around people with power and influence will open your eyes to how they think and, more importantly, how they maneuver. If you don't see examples of people you want to emulate, you're not likely to become like them.

At 25, Erin became the Director of Development for Northwestern Hospital, Chicago's premier hospital. She got the job by saying yes to a babysitting gig while working as a receptionist at a leading real estate firm. The mother she babysat for turned out to be a very influential and well-connected donor at Northwestern. She saw potential in Erin and brought her on board to manage the Lynn Sage Breast Cancer Foundation, setting Erin on a path to becoming the youngest Director at Northwestern and overseeing all 17 of the hospital's charitable organizations. 

The hospital's board members and donors were Chicago's movers and shakers in finance, medicine, and law. Erin’s work involved building close relationships with them to ensure continued donations.

Erin then went on to work in the Private Bank at JP Morgan, closely working with high-net-worth families with typically $100M+ net worth. As their banker, she became a trusted insider, understanding all the family dynamics. She recognized that these high-net-worth families were as concerned with their legacies and families as with their market returns. Erin served as the quarterback, catering to their company, personal and financial needs, advising on wealth management and interpersonal matters.

Being exposed to so many powerful and influential people at an early stage and learning how to maneuver in those spaces by grasping their priorities and how to serve them was invaluable.

We've all heard the metaphor, 'You are the average of the five people you spend the most time with,' and Erin took that to heart. She leveraged her experiences with those powerful and wealthy people and went on to build a great network.

Building A Network

Erin attended business school between her roles at Northwestern and JP Morgan. Upon leaving Northwestern, she sent letters to each of Northwestern's board members, explaining her decision to further her education and including a personal note. This gesture showcased her authenticity and helped maintain the relationships, many of which remain strong 30 years later. 

"Staying close to your network is critical. People who are very successful build these really meaningful networks with lots of tentacles," Erin advised.

Her expertise in relationship-building eventually led to one of the most transformative connections of her life.

Transformative Relationships

Transformative relationships are relationships that significantly impact your life.

Meeting Jenny Just, a self-made billionaire, has been a transformative relationship for Erin.

While working at JP Morgan, Erin was asked last minute to attend a meeting to fill in for a sick colleague. Not as prepared as she usually was on the topics of the meeting, Erin chose to take a different approach: building a genuine relationship.

When Erin entered the meeting room full of male bankers, she decided to sit next to the only other woman there, knowing she should find a commonality. They started talking about shoes and quickly became friends.

Fast forward 25 years, and Erin has remained close friends with Jenny Just and her husband and co-founder Matt Hulsizer. She's worked in several of their businesses, most recently running Poker Power as President.

When I pointed out that in today’s culture some women might shy away from choosing to talk about shoes with a high-powered woman, fearing it would seem stereotypically feminine, Erin said, "I don't think you should shy away from stereotypical topics, particularly in a business setting. I think whoever you are, authentically being you and finding that overlap with another person, that's what they remember. Also, we both really liked shoes," she laughed.

Erin continued,

"People often rush to get the deal done, rush to the transaction, and in fact, that's the worst way to build a longstanding relationship. It starts with connection, familiarity, and shared experiences. That way, people actually want to come back and talk to you again, since it takes a few times to decide if you're the right company or vendor for them anyways."

Erin's approach highlights the importance of building genuine connections, as you never know which one will become transformative. Transformative relationships are the main reason you'll rise to the top without existing power, influence, or wealth.

You can seek them out, they can happen serendipitously, or you can combine strategy with a touch of serendipity by placing yourself in environments where you're more likely to meet someone transformative.

While it may have been serendipity that Erin's boss asked her to attend the meeting with Jenny and Matt, it was Erin's understanding of how to connect by finding a commonality and being personable that made the difference.

Building Credibility

Credibility is the foundation of why people choose to work with you. It encompasses your trustworthiness, capabilities, and adeptness, and is often shaped by your past experiences. 

There are numerous ways to build credibility, such as earning accolades or referrals. However, being strategic about who you work for, and work with, is one of the most effective tactics for intentionally building credibility.

Erin explained the significance of having prestigious institutions on her resume, emphasizing their substantial impact. "When you have a stamp of approval from two top institutions, you get second-guessed a lot less," she revealed.

This is why she greatly values her business school degree from the Kellogg School of Management and her previous Vice President role at JP Morgan. 

Erin advises young professionals to seek opportunities at well-respected firms early in their careers. 

"I always tell my kids, get the very best that you can," she shared.

For instance, Erin's recent guidance to a mentee underscored her belief in the value of these ‘stamps of approval.’ When mentoring a college senior torn between a startup and a consulting firm, Erin recommended starting with the consulting firm. "Go to the consulting firm for two or three years, get that stamp on your resume, and you'll have far more opportunities," she suggested. 

Her advice surprised the mentee, given Erin’s extensive work with startups. However, Erin believes the experience provided by top firms will offer long-lasting benefits throughout one's career and set a foundation for understanding best practices and how highly successful firms operate.

Another tactic Erin employs to build credibility is deferring to experts in fields outside her experience.

To illustrate, when designing and launching Poker Power's curriculum, she relied on expert women poker players instead of attempting to design the lessons herself. "Adhering to these high standards helped to establish our credibility within the industry," Erin noted. Her approach demonstrated the effectiveness of leveraging others' expertise and credibility to build your own credibility, especially when you are not the de facto expert.

Being Strategic

One reason I work with leaders and share their journeys is to show that it's okay to be strategic about things often left to chance: meeting people, building friendships, and finding new opportunities. 

The phrase 'fairy godmother complex' became popular in recent years since it pointed out that many of us believe, like Cinderella, that if we work hard, our fairy godmother will notice and grant us a better life.

The truth is, the leaders I work with set their intentions clearly. They explicitly say and set intentions around goals like earning a lot of money, achieving the top position at their company, creating a legacy, and being remembered.

Having a plan determines your focus, and taking calculated risks can lead to significant growth and opportunities.

Erin made a strategic move early in her career, and it was a bet paid off. 

Initially, she planned to stay in healthcare management after business school since she already had experience in the field. However, in business school she learned how much earning potential there was in finance so she switched career paths. 

By openly acknowledging her desire to make a lot of money and pivoting her career based on that goal, Erin was able to build wealth. This later enabled her to support women in business, her primary passion, through investments and advocacy for closing the earnings gap between men and women.

Reflecting on her journey, Erin shared that similar to playing poker, not every hand is a winning hand. It's about how you play the game. 

"I didn't come from significant wealth and I worked for everything that I have. I was smart in how I leveraged relationships. I was smart to go to a top business school. I was smart to go to a top financial firm. I had a decent hand and I turned it into a really good hand. But I think it's because I've also failed a lot. I've made a lot of mistakes in my personal life. I've had two marriages. I find motherhood challenging. I've had to actually really work at how to be a mother. It's just not an instinct that I have. So I read a lot of books and I talk to a lot of people," Erin disclosed.

One of Erin's favorite strategies is always saying yes to new opportunities. She believes in pushing herself on the risk spectrum, not out of naive ego, but because she knows that by continuing to say yes, she will also make mistakes. However, she has confidence that she will learn from the experience, become better because of it, and keep moving forward.

Moreover, Erin has instilled this mindset in her daughters, teaching them the value of being comfortable with discomfort. She believes that this ability opens doors and builds relationships that lead to significant opportunities. 

Erin encourages her daughters, "Get comfortable being uncomfortable, because it's one of the greatest ways to develop relationships that lead to power and influence. I had to learn that just because you work really hard, produce excellent deliverables, and do all the right things, most people don't notice you unless you can articulate what you've accomplished and why it matters.”

Leveraging a Catalyst: Her TEDx Talk

Building momentum is a process, and certain events can act as catalysts, such as creating a body of work, receiving significant acclaim, or doing something noteworthy and highly visible. These significant instances can catalyze momentum both personally and for your initiatives.

In 2018, Erin gave a TEDx Talk titled "Equal Pay for Equal Work: From Head Nodding to Hand Clapping." Within it, she shared a personal story about receiving her first bonus at JPMorgan and not knowing she should ask for more. 

That missed opportunity taught her the importance of negotiation, a lesson she now applies in various aspects of her life, and she often advocates in her speeches "Just ask for more. Get used to asking for more." 

That TEDx Talk was instrumental in establishing her as a credible voice in gender equity policies and corporate recommendations. Since then, she has participated in over 200 interviews, podcasts, and conference panels. 

"Having a public platform to share my ideas has had a multiplier effect as more and more listeners tune in, I have more opportunities to reach new audiences," Erin revealed. 

Reflecting on her early days of public speaking, Erin indicated she accepted every opportunity, even if there were only a few attendees. Each speaking engagement built her confidence, allowed her to solicit valuable feedback from attendees, and often led to further invitations when an attendee was inspired to introduce her to their organization. 

Starting with small women's groups and college campuses, Erin now regularly speaks on global stages and is featured in top-tier publications.

Erin again touted the importance of saying yes, sharing "I never knew where my next break would come from, so I said "yes" to everything, especially the things I didn't know how to do." 

The TEDx Talk provided Erin with a legitimate platform, leading to numerous speaking opportunities and even a teaching position in management and strategy at a local college. This opportunity directly resulted from a connection made through her TEDx Talk.

Challenging the Status Quo

Throughout her accomplished career, Erin has focused on challenging systemic issues, particularly in male-dominated industries. When asked about a system within her industry that should be changed and how it came to be, Erin reflected on her experience:

"For over 25 years, I've worked in male-dominated industries from banking, to esports, to gaming. Choosing to be in rooms where I am the only one who looks like me is a challenge and also an opportunity to shift systems to be more inclusive. Poker is a great example as only 5% of the professional players are women and even the most accomplished aren't always welcomed at the table.

The stereotypes of where poker is played, be it smoky basements or opulent casinos, does not feel inviting to most women, and in fact, is quite intimidating.

I believe there are three systematic gaps women face in the poker world which parallel the challenges in the business and venture capital world:

1. A knowledge gap
2. A risk-taking gap
3. A bankroll gap.

Until women learn the rules of the game, have the experience to play aggressively, and have control of enough money to engage at higher stakes, the playing field in poker rooms, interview rooms and board rooms will remain uneven," Erin stated.

Erin has tackled these challenges by advocating for greater inclusion and equity.

She believes that shifting the status quo is everyone's responsibility, especially those in positions of power.

She outlined her approach to creating change:

"These are the three steps I use to create change when met with resistance--whether it's encouraging more women to think like a winning poker player, to negotiate for pay equity, or to seek recognition and advancement opportunities:

1. Gather data. Know the market and your place within it. You can't advocate for more until you know where you currently stand against the competition. Also, ask a close friend or colleague to candidly assess your weak points so you can address them proactively.
2. Get comfortable being uncomfortable and practice taking risks. You can do so in a meeting by speaking up rather than letting someone else voice your ideas, or you can seek public speaking opportunities by serving on a panel at a conference, or you can be the one to correct a micro-aggression in the workplace--these are all beneficial ways to push yourself further out on the risk spectrum.
3. Remember that 'no' doesn't mean 'never.' Keep asking for that raise, that promotion, and that stretch assignment. You will increase your confidence every time you ask for more, which better positions you to hear the 'yes' you deserve."

What's Ahead for Erin

When we spoke, Erin was in the process of selling her house and everything in it, along with 100 acres of land. She was ready for the next journey and wanted to start afresh in a new city which was yet to be decided.

A beautiful aspect of Erin's career path is her evolution from a structured corporate environment to embracing the dynamic and frenzied world of startups, to now sharing her personal advice and life lessons with the world. 

When asked about her future plans, Erin shared her desire to continue embracing new challenges and learning opportunities.

"Every new job I've ever had in my life has been something I didn't know how to do in some way. For what's next, I want to pick something that I haven't already figured out. I want to learn."

Erin's next role will likely be in startups, given her passion for the entrepreneurial world and her commitment to supporting women in business.

While she continues to discuss poker and closing the gender gap, she is increasingly focusing on sharing her wisdom about life and parenting. "I do a lot of public speaking, but I'm not really talking about poker as much despite playing it regularly now. I'm talking about how to be successful, how to be meaningful to your own life, to your own family, and the lessons I've learned."

Erin also shared with me a personal anecdote, "I made a LinkedIn post a couple of weeks ago when my youngest graduated from high school, which is all about the advice that I keep saying to my girls, and maybe all moms do this, I don't know, but I feel like teenagers are so hard to connect with. So I send them these little posts that I make up on my own, hoping that, you know, maybe one 100th of them actually sink in at this young age. I spend most of my time now giving back, just thinking about how I can help other women particularly."

Erin’s early exposure to power and influence, along with strategic moves and calculated risks, has prepared her to challenge the status quo and support others in their journeys. As Erin embarks on this new chapter, she continues to inspire with her dedication to lifelong learning, her commitment to empowering others, and sharing her acquired wisdom.

Want to see Erin in action?

• Watch her TEDx Talk here
• Read her interview in Forbes here
• Listen to Erin’s episode ‘Negotiate Fearlessly’ on the How She Does It podcast

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