Connie Steele I Future of Work Expert

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Ep. 139 - When It’s Time to Move On: Familiarity, Discomfort, and Identity - with Sara Conde

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Part of the reason I share this podcast is because I think there’s a lot of value and inspiration in hearing people share their stories. Sometimes we get that from authors, sometimes we get that from mentors, and sometimes we get that from friends. And today’s guest is a friend who I’m proud to say has been an inspiration on my own journey.

Sara Conde is a sales coach and the Director of New Business at Collective, an online back office platform designed for Businesses-of-One. She has a journey that reminds us it’s never too late to try something new, and I think it’ll be inspiring for anyone who has ever felt a little stuck in an uncomfortable point in their life. Because even if something is a little uncomfortable, the familiarity can feel safer than taking a leap into the unknown. But if you sit in that discomfort and discontent for too long, it can really add up.

When It’s Time to Move On

Sara spent 14 years of her career doing something that is increasingly uncommon: working within one company. It was comfortable, it was an important part of her identity, and the people there had supported her. So when it was time to move on, when the organization was no longer the right fit for Sara’s life, that comfort and inertia made the transition just that much harder.

Although she left college a little directionless, and after a few short stints at jobs that weren’t a fit, Sara found a home at an organization that supported independent consultants with their back office. She loved that the company’s success was aligned with the success of the consultants they served, allowing her to genuinely help them thrive. Sara’s own career flourished as she not only had the chance to work in a variety of roles within the organization but she also was able to build a sales team from the ground up.

This job became a critical part of her identity. But when she realized that the organization was no longer a fit, it was challenging for her to consider new opportunities. 

The Moment of Transition: Getting Comfortable Being Uncomfortable

Sometimes it takes an outsider’s perspective to help you also see where you are in your life no longer aligns with who you want to be.

Having grown up in one company, her identity had been defined by it. She had been successful there, they had supported her, but there was self-doubt on whether she could have the same impact elsewhere. It was that fear of the unknown and fear of failure that was also holding her back. 

She had an epiphany when she started her own LLC on the side. She started to gain confidence in her own expertise and she got the feedback to validate that. But she also realized that she wasn’t leveraging everything she’d learned to her fullest potential. 

Sara understood she had to nurture this growth mindset to overcome the fear of change that holds so many of us back; she had to reframe her career journey as a learning process. And in the process of testing, trying, and failing forward, she started to get more comfortable with being uncomfortable.

Struggling with Mental Health

Sara also shares how mental health impacted her along this journey. We haven’t talked about this topic on the show much, but I think it’s a really important perspective to hear about when we’re discussing these complex transitions in our lives, some of which we can control and some we can’t. Because a lot of people struggle with their health at different periods of their life, but one of the things that can make those periods of our lives even harder is that we don’t always talk about what it’s like, and that can make an already difficult experience that much more isolating.

But I want to let Sara tell that story in her own words. We talk about it in the episode, but Sara shares her story in a little more detail here:

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I want to thank Sara again for sharing her story with us. I think it’s a really empowering reminder that we do have control, in our lives and in our careers, even when we’re starting to feel trapped. Whether you just feel stuck in your job or you’re struggling with your health, it’s easy to start feeling a little alone and hopeless, it’s easy to just stick with what’s familiar even when it’s uncomfortable, and that just makes change that much more difficult to deal with. So I hope Sara can serve as a reminder and some inspiration that we’re not alone on these journeys, and we have the ability to create something better for ourselves.

Definition of success

  • To work on things that excite me and be in a work environment where I feel accepted for who I am. 

Best career advice

  • Understand your people beyond their roles. Learn what they want to do in the future and coach them to get there because you’ll get more engaged and loyal employees in the end.

Key Takeaways: 

  •  Comfort and loyalty to an organization can often keep individuals stuck and create hesitation about making a change. But it’s not a negative when people realize they want to move on — it just means where they are isn’t a fit anymore. It isn’t about loyalty and you can’t wait for an organization to change.

  • We have to get comfortable with being uncomfortable. Our lives change so rapidly, internally and externally, and everything gets harder when you resist that change.

  • One way to mitigate the fear of risk or change is to start by piloting small test-and-learn projects. Sara started a side hustle that ultimately fueled her, gave her confidence, and helped her figure out what she’d like to do next.

  • It’s easier to weather the discomfort of change when you have an accountability partner.

  • Everyone’s path looks different and we shouldn’t force everyone — or ourselves — to conform. It’s easy to fall into the trap of trying to emulate someone who is successful or is where you want to be, but we’re all working with a different toolbox.

  • If you’re struggling with your health, it can feel isolating. Try to remember that you are not alone in your struggle and remember to look to support and community where you can.

  • Take a break and take care of yourself before you don't have a choice.


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