Episode Summary
You have to work hard to get your dream job. You also have to continuously learn and be ready to take certain risks to reach your goal.
However, despite a strong desire, many people are insecure and afraid to step into something new. They are lulled into the routine of their current job, and although they are aware that they will not progress there, they remain in their comfort zone and do not make their career into what they really want.
Megan Dimmer is someone who has taken risks to make her dreams come true. She made decisions that may seem frightening to some. But, those calculated risks are why she is the CRO at Esellas today.
In this episode of Taking the Lead, Megan gets into her career journey and describes her transitions through it. Megan and our host Christina Brady discuss career planning, taking career risks, and the importance of having your life team.
Guest Profile
- Name: Megan Dimmer
- What she does: Megan is the CRO at Esellas.
- Company: Esellas
- Noteworthy: Megan's experience spans over two decades and across industries — from technology to professional services. She spent the first chapter of her career successfully selling and leading Fortune 500 technology sales teams. She then pivoted and ran an industry-leading professional services firm. Today, she is the CRO at Esellas.
Key Insights
- How to make your dreams come true? For most of her early career, Megan was a Fortune 500 tech sales leader. She left that job to move into professional services. Although it seems like a potentially scary transition, Megan achieved her dream — becoming the CEO of the largest multifamily architecture firm in the world. Today, she is the CRO at Esellas and reveals her secret to success. "The playbook is having confidence in that dream and in that goal and being willing to step outside of whatever box you put yourself in or someone else put you in. To say, 'I deserve to get there. I've earned whatever place that I'm in. I feel like there's more out there for me, and if I don't take this chance, if I don't take myself out of the comfortable spot and risk it, I may never get there.'"
- Your life team can help you take the leap. Anyone who has dared to take a risk and try something completely different — even though they eventually succeeded — will say it was not easy. According to Megan, if you have your life team, you will feel safe enough to take risks and ultimately succeed. "A life team that you know you can pick up — you can phone a friend. And literally, I'm not talking text, I'm talking about picking up that legit old school phone and dialing them up and saying, 'This is what's going on.' And there's no judgment on the other end. There is active listening — and the expectation is you're going to do the same for them. But have that [life team], have confidence in yourself, and have an internal conversation that says, 'I'm making this decision consciously. I know that there will be tough spots. I'm surrounding myself with people before I make the leap.' And always have your legal team involved as well, if you have those resources."
- You should plan for potential failure when taking risks. When you make an important decision in life, you should analyze it well and see both the good and bad sides of the move you plan to make. Megan notes that if you're going into something new, you have to plan for the pitfalls. "If you are truly weighing the risk, you have to think about the potential. So, can I afford it — and I'm not saying only financially — but can I afford it as a human? Do I have what I need to overcome a potential failure? And if I do, if I've got the people, if I have the resources, if I have the knowledge, if I understand myself well enough to take that risk, then take the risk. If I don't, maybe now is not the time. Maybe I need to build that life team."
Episode Highlights
Is There a Women’s Network?
“I’ve done some research on the topic, and we frankly are not as good at building a network as we should be. We build rapport, we build relationships, and we nurture,
but we don’t build the network. Why is it called a boys’ club? Because they have their network. So, why don’t we have a girls’ club or something different from a boys’ club? I think we need to get better at it, but the only way we get better at it is if we help each other, and if we are intentional about building that network, and we say to ourselves, ‘I know I need it.’ It’s not going on LinkedIn to reach out to a thousand people, just to have a thousand people as your followers. Those people, by the way, when you need something, and you call them, they don’t answer. So an intentional commitment to building a true network of people that know who you are and vice versa — that I think is something we need to work on.”
The Advantage of Diversity in the Group
“The only way you get out of your bubble is if you’re forced out of it because it’s warm and safe. And a lot of people groupthink, by the way. It’s vomitous to me to be in a room of people who all think the same way. And that’s what you’re doing. You’re creating a lot of people who are, ‘Yes, yes, yes.’ And sometimes, when your ego gets in the way, you want people around you to say, ‘Yes,’ and you’re like, ‘I have this great idea. Don’t you think?’ Versus, ‘I have this idea.’ But all of these people from different backgrounds, different experiences — true diversity. Ultimately, this idea may become a unicorn if only we tap into others. So I think it goes back to, ‘If I go to an unsafe place, am I going to be okay? Is my career going to leave the track if I happen to make different decisions about the people I bring in to the team? Is this organization going to support me if I bring in people that are unlike others in the organization?’ And, by the way, those people have to feel included.”
Megan: Your Echo Chamber Can Stop Your Progress
“I honestly was in a toxic situation at one point in my career. And I was toxic at home; I wasn’t the best mom; I wasn’t the best significant other. I knew it, but I was like, ‘You’re doing great, keep up the good work, and you’re such a good leader. And I’ll tell you what — I was an asshole sometimes, and I didn’t even realize it. I look back, and I say, ‘Oh my God. What if that person was my leader?’ That’s not a leader. And so, the feeling is that I could have done things so differently if my chamber was like, ‘Look in the mirror. Do you see what’s going on?’ And that’s so threatening when you have to tell somebody that you love, when you have to call their kids ugly, that’s really, really uncomfortable.
I try to live in this radically candid environment where every opportunity to show somebody that I care about them, I will show them that I care about them personally so that when the moment comes when I have to challenge them directly, I’ve earned the right. I’ve made three positive deposits so that I can make that one withdrawal. But don’t worry, more positive deposits are coming in a different conversation.”
