Transitioning & Thriving in Tech: Overcoming Imposter Syndrome, Navigating Layoffs

Continuing our conversation series on transitioning and thriving in tech today, Worklife joins with the top founders and creators in the industry to bring you everything you need to know to build success. Didn’t get a chance to join our Zoom chat? Don’t worry! We are bringing you all the highlights of our convo with three of the leading minds in the industry. Join us as we gain insider knowledge on transitioning and thriving in tech today. 

Open the News app on your phone and swipe over to the tech news tab (or don’t, we won’t blame you). 

It’s bad, isn’t it?

Every news cycle brings more layoffs, downsizing, and pivoting by big tech (i.e., Microsoft and Spotify), talking heads can’t decide if AI is revolutionary or competition, and recession fears loom.

We’re here to tell you, it isn’t all doom and gloom. Tech jobs are still in high demand, AI is already creating jobs, and all those mundane tasks of work life are slowly going the way of the CD-ROM.

You might want to ask: if the biggest names in the industry are transitioning, are you? 

At Worklife, we tapped some of the most exciting creators, thinkers, and founders in tech today to teach us how transitioning and thriving in tech is the key to longevity in our industry. Meet our speakers:

• Yari Blanco, founder of theGIRLMOB, former leader of multicultural partnerships at Twitter
• Katie Chen, CEO and founder of Kairos
• Suezette Robotham, Senior Director of Executive Recruiting Equality Strategy for Salesforce

Our host, Michelene Wilkerson, leads the conversation, as our guests share everything you need to know when transitioning and thriving in tech. We cover:

• Transitioning and thriving in tech by standing out
• Finding balance when transitioning and thriving in tech
• Redefining performance while transitioning and thriving in tech
• Transitioning and thriving in tech as a founder
• Navigating imposter syndrome when transitioning and thriving in tech

Transitioning and Thriving in Tech by Standing Out

Michelene Wilkerson: What does it take to stand out in tech today versus in previous years?

Katie Chen: [Become] multilayered. If we look at the recession in isolation, it's not the clear picture. There's the pandemic, and then we have quiet quitting or the Great Resignation, and then we have this recession.

So I think in the context of things that people off the back of recession are really realizing [is] how they want to live and work. Not just to purely work. Now people are demanding more respect—and, I would say, respecting themselves—to be like, “Who am I going to be in connection with work?” 

And so for us as a young company, especially recently—making hires and going through so many candidates—we realized we really needed to have that together in order to appeal to candidates, as a young startup, to even be thinking about, “What is our maternity leave policy?” For us, it's thinking through everything, our benefits, all of that in order to even stand out and compete, especially in a market where people are looking for stability. 

Wilkerson: I'm also curious if anyone has thoughts on the employee side and what it takes to really just stand out in a hard time?

Yari Blanco:  I would say for someone that's starting out—I'm thinking of folks that are associate levels or coordinators that are coming in that I've worked within the team that I'm on—I'm always like, make sure that you come up with something that's uniquely you, that you feel passionate about. Whether that's like a newsletter that you do biweekly that goes out to the company or to the team or you know, you're jumping in to be like, “Hey, can I help you with this recap?” 

I started my career 16 years ago, and [these things] still stand true. Like raising your hand to help will always keep you top of mind for two reasons: 

1. They're paying attention to what's going on across the team.
2. They have an interest in learning.

And the opposite is true. If you're like, I'm just doing the job that I was hired to do, then you're not gonna be picked to be part of projects or to help a certain thing. 

I would say something that I've done is really owning some of my superpowers. I'm bilingual, so I speak English and Spanish. I work within music, and so immediately I was like, how do I make my mark at the company within Latin Music to make sure that those artists are getting the support they need? I'm uniquely positioning myself. I have relationships with those companies, talent, management, and their publicists.

Figuring out your niche, but also the thing you love to do, is a really good way to be able to differentiate yourself from your colleagues.

Suezette Robotham: I think it's the intersection of what both Katie and Yari have mentioned, right? It is: 

1. Being clear on your purpose 
2. Not being afraid to be an expert in owning your niche. 

You become the go-to for specific things, right? But it's also making sure that you're becoming an expert in a space that you're actually very passionate about and committed to. It's a purpose alignment.

I tell people my major is talent acquisition, but my discipline is:

• Diversity
• Equity
• Inclusion

I've managed to carve out a niche within the talent acquisition space and become an expert in how we really think about building our diversity recruiting strategies. 

My life has been committed to creating access and opportunity for others, right? Because the other most important piece about it: it's insufficient to be an expert and to be doing purpose-driven work that you don't actually have a narrative about. 

How do you craft the conversation and tell the story of not only the niche that you're the expert in, but why you do that work and how you'll continue to bring and add value to what a company's bottom line is?

Finding Balance When Transitioning and Thriving in Tech

Wilkerson: Three things I'm getting from what all of you are saying is:

1. Bringing your whole self and all the pieces that make up this whole that is you.
2. Owning your expertise.
3. Being able to translate that into something results driven.

There's this tension between just showing up for the job, because so many people feel their jobs are not valuing them. Even if they do crush their soul to do the work. 

How do you balance this idea of rest and taking care of yourself, and rocket-shipping all the way? Is there a balance?

Blanco: I have a lot of feelings about this. I think first and foremost, where you live really makes a difference in the US. I literally was just talking about this on my social media. In the U.S., we are so driven, we're so driven by output. And if you live in cities like New York City as someone that’s a native New Yorker, the hustle is real.

If you don't have 10 jobs, if you're not doing 20 creative projects, etc. That is bananas. I'm so happy to see, especially Gen Z, talk more about, “I am not a machine that's just meant to have this much output.”

I think in the U.S. it really matters how good you are at creating your own boundaries. And again, I think specifically for me as someone that comes from entertainment in New York City, that's really hard, right? Because in New York, everything's like, “I needed it yesterday.”

So if you don't have boundaries with yourself outside of work with your family, with your friends, with yourself, then it's really, really hard to have those boundaries at work and to be able to say no to projects that you don't have the bandwidth for, or to tell people like, “Hey, two weeks from now I'm gonna be going on vacation, I'm out.”

Here in the U.S. it's like you're only as good as your next project. We don't even celebrate the wins. I really do think that from an individual level, it starts at our own boundaries with self and with our own interpersonal relationships.

Us talking about it in spaces like this with our friends and encouraging each other, that spreads and echoes and then, hopefully, companies start to listen.

One of my friends works at [a popular music-streaming company]. She was like, “Oh my God, during this week people are gonna lose their mind. It's a company-wide wellness week, and we're all gonna be off on our own or doing company wellness related things.” I'm like, “YES.”

We need more companies to do this because if we leave it to the US government, that's just not gonna be the case. Those kinds of regulations are just not gonna happen as quickly as we need them.

Redefining Performance While Transitioning and Thriving in Tech

Wilkerson: On this topic of balancing rest and ambition, do you think high performance is being redefined during this time? And if so, what do you think the new rules of high performance look like? What does that look like to perform highly, especially when you're new into the space and trying to build your individual brand?

Robotham: I have a couple of reactions to it. I know that the tone leadership sets about rest sets a tone for a team or organization, right? And so, as a leader, as a manager, one of the things that I prioritize for my team, just as we at the beginning of the year set OKRs we're setting our goals, we're setting our key priorities and agendas. I very much tell my team at the beginning of every quarter, I also wanna see you put PTO and time off in the calendar at the same time.

We're having active conversations around, “Here's where the work is, but here's where opportunities for breaks and rests live.” Because, at the end of the day, you can't be high performing and functioning [while] broken and tired. I need people at their best. 

When I think about productivity, I think a lot of that is also how you are bringing your team along the journey. And so again, another element of leadership is how are you actually really anchoring and helping your team to understand what the goals and priorities are and what their role and responsibility is in achieving those things so that folks wanna understand how they help to drive the bottom line and what their contributions need to be. Then, also to that broader sense of, “This is how we build in breaks and this is how we think about rest.”

What I do with my leaders very critically is set our goals and objectives together. For instance: 

1. Let's make sure that it makes sense. 
2. Let's pressure test it.
3. Let's go back to my boss and make sure that these goals make sense.
4. If they don't make sense, let's not be afraid to revise and talk about why the goals need to be revised.

The challenge with productivity and the conversation that we are having is there's a lack of accountability around manager accountability. There's a lack of conversation around how managers are actually leading and guiding their teams and showing up as leaders and not just managers.

Productivity in a vault is not productivity at all. So I think there's a broader conversation we need to have about people and productivity, and not just productivity by itself.

Transitioning and Thriving in Tech as a Founder

Wilkerson: What would be your advice to first time founders or people thinking about starting up? How should they prepare for that mentally, emotionally, emotionally, spiritually? 

Chen: Check whether you're an optimist first. Because of this recession coming up, the story I tell myself is, if you can make it through a recession, if you could thrive a little bit—not like full thrive, but thrive a little bit—you've got something. This is the ultimate test. 

So, as an optimist, I'm like, yeah, bring it on. Let's figure out if I could, if I could be a cockroach and survive this. [You need to]:

• Check if you're an optimist.
• Check if you have the support around you to [maintain] resilience. 
• Check yourself.

Cuz the other thing is if you don't figure it out, you end up working it out on your team, and they don't deserve that.

Experiencing Imposter Syndrome When Transitioning and Thriving in Tech

Wilkerson: How do you overcome the imposter syndrome when you make the leap, the transition, or continue climbing higher? What keeps you grounded and not catering to imposter syndrome, if that's something that you've experienced?

Robotham: I don't get imposter syndrome, and people look at me in shock when I say that. But at this point in my journey and this point in my career and this point in my life, this is who I am as a Black woman. I have the skillset, the ability, the talent, the experience that has put me in every single seat I am.

And organizations are just as blessed to have me as I am to be in that seat. I get very cautious around titles because I think sometimes we very quickly wanna be like, “Oh my gosh, I have imposter syndrome.” And we take the onus off of the organization. 

The fact is,they may not actually be creating a culture or have a culture that is open and inclusive to all types of styles and all types of ways of being. And so I like to hold up the mirror and ask, “Are you an imposter?” 

Can't there be a learning phase? Isn't there an opportunity for you to really build a fundamental understanding of where you are without needing to be labeled an imposter? And if a culture is perpetuating the idea that you have to feel like an outsider before you belong, then what is it about that culture that needs to change in order for everyone to feel welcome, to learn and grow and develop and thrive at the company or organization?

Blanco: I would say 95% of the time, I'm good. Everything Suezette just said is like, “Y'all hired me.” I know you Googled me before you hired me. Whether it's for a full-time job or a conversation like this. Like I know you did your research, so you know what you're getting. You know what you're walking into. You're gonna get the door knockers, you're gonna get the bright nails, you're gonna get the outspoken person. That's just who I am. 

So 95% of the time I'm good. I will say the other 5%, it shows up in two ways:

1. When I am the only [minority] in the room.
2. When I'm invited into certain rooms again or into certain conversations with folks where these people are so far ahead into their career.

As a woman I'm like, “I'm bringing all the people with me.” And so there is a self-imposed pressure to make sure that the work that I'm setting up or the way that I'm showing up is creating space for other people that are trying to get in the room.

Something I've learned the last few years that has become very potent for me is: you are always a teacher and you are always a student.

Just because I'm younger than somebody—even though I have 15 years experience, they might have 20, they might have 30—it doesn't mean that they don't have things that they could learn from me. Whether that's my point of view on something, fresh eyes on something, my lived experience—whatever that is—anytime that bubbles up just that little bit, I'm like, oh yeah, I totally have something to offer here, no matter what the room looks like. I hope that's helpful for people, cuz a lot of times we think that we don't have something to offer. But again, you're always a teacher and a student and you just get to play both sides.

Chen: For me, I've spent the majority of my career being a graphic designer, then becoming a digital product designer. And now I have this title called CEO, and imposter syndrome is very real for me now because people ask, “What do you do?” And then in that moment I always feel like I'll go one way or the other.

I'm still getting used to saying I'm the co-founder, CEO of a company. Part of it is reminding myself that I've worked with a lot of people and the thing is: no one really knows what they're doing, but everybody has the foundation to figure it out.

Lately I've just been really reading as much as I can, from everything about product management [to] books or blogs or newsletters people have written. [Ways] of battling my imposter syndrome are:

• Studying up
• Asking questions
• Reaching out to my investors and advisors
• Being open and vulnerable in those moments

If I don't ask, I'm gonna end up wasting my time and I'm gonna put my company and my team in a bad position. It's just like really leaning into [admitting], “I don't know, and I'll figure it out”—just put myself out there and see who would help me. And that's a way of battling imposter syndrome: just lean into it.

Wilkerson: Even though you all said it in different ways, continuous learning, continuous growth is a major theme, and it's something that has prepared you for the levels and the mountains that you all still continue to climb. You're doing the work both internally and to level up on the skills, and doing the work that you need to do to be at the level that you're at.

I think that's a really important key point to drive home. It's not, “I don't have imposter syndrome.” It's, “I'm doing the work and this now creates a secure base inside of me where I can transition and thrive anywhere.”

Discover More Creatives That are Transitioning and Thriving in Tech

Enjoyed this discussion? You can view the entire interview here.

Want to discover more founders and creators that are transitioning and thriving in tech. Visit our blog to read more:

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• Meet the 18 Content Creators Helping Startups Onboard New Users
• Experiencing Creative Burnout? This Creator Is Here to Guide You Through It
• The Future Founder is Creative: How Creative Entrepreneurs are Revolutionizing Work
• Celebrity Entrepreneurs and Brands, a Growing Cohort