Have you ever wondered why so many people fail to land their dream job after attending a boot camp or taking an online course? In this episode of Unlearn Podcast, Barry O’Reilly chats with Sarah Doody, a UX researcher and designer, and the founder and CEO of the Career Strategy Lab, a program that helps UX and product professionals at all career stages navigate the job search and articulate their skills and experience to help them grow. Sarah talks about her journey of designing her career and helping others do the same. She and Barry discuss the need for ongoing career development, the importance of setting boundaries, and why systems and design thinking is important in building a successful business and career.

Designing Your Career

“When I think back, I realized that I’ve always been designing my career,” Sarah remarks. She describes herself as a systems thinker who can spot problems and opportunities in sales, marketing, product, and engineering. However, her multi-talented nature often meant people didn’t know what to do with her, and she had to design her own roles at different startups. Barry recalls how when he joined ThoughtWorks in 2010, only engineers were considered essential, and designers were struggling to find a place. He comments that the talent to design from experience to prototype is a core skill, and one of the main reasons his former colleague went on to become CEO of Thoughtworks. “When I think of design, it’s not like just designing products, it’s designing processes,” Barry comments. “It’s designing onboarding experiences for people, …to know what the needs are, and then to create a solution that creates this great experience.” [Listen from 2:10]

Learn about designing a career strategy with Sarah Doody, founder of Career Strategy Lab, and discover job search & skill articulation.


Designing Your Life

It’s hard for many people to pivot away from their established life into creating the life they truly want for themselves. Sarah, however, came to that inflection point and decided to take the road less traveled. She left her full-time job without a plan but with some savings. She focused on building her network and figuring out what her offering as a freelance UX designer would be. She structured her consulting services into three clear options, which helped her clients cut through the noise and get to meaningful conversations. Think of consulting or freelance as a fast food restaurant menu with a limited number of items, she advises listeners. “I think a lot of people go into consulting or freelance and just say, oh yeah, I do UX. That’s walking into Costco with no list,” Sarah says. “I always say to people, if you want to do consulting or freelance, you kind of need to think of what is your fast food restaurant menu – like your in and out menu – one of those restaurants that doesn’t have 50 things on the menu – that has three.” This approach helped her land her first few clients without a big audience. “When I didn’t have a huge audience, I had to make sure that if people did stumble across me, they had a decision right in front of them,” she says. Barry agrees that having clarity on what you do is essential and that starting with a narrow focus is often more effective than trying to do everything. As your career evolves, you’ll naturally gravitate towards certain industries or things within your profession. [Listen from 11:45]

Career Strategy Lab

Sarah shares her journey from UX consulting to building her education business, Career Strategy Lab, which helps job seekers and professionals find purpose, reward, and recognition in their careers. She describes the evolution of the lab, from creating online classes and in-person workshops to running a six-month career incubator. “We go through creating all kinds of the assets you need for your job search,” she tells Barry. “It’s a joy to watch,” Barry remarks, “but also to see the results, creating social mobility for all these people, helping them figure out what they actually want to do and enjoy, and then actually creating better opportunities for them. It’s tangible. Not many people get to build products where they really can see how they’re helping their users.” [Listen from 23:20]

Sarah’s Unlearning Moments

Barry asks Sarah, “What have been some of the biggest aha’s for you along the way… or something that you thought would work out one way but actually turned out the other?” One of the biggest insights she had, Sarah responds, is that not everyone will actually follow through, even though they’ve been given all the “ingredients”. She emphasizes that everybody has to take personal responsibility. “The other side of it is recognizing that people need the mechanics and instructions, et cetera, to do things,” she continues. The pandemic has affected people’s sense of isolation, self-consciousness, and low confidence, making them nervous about job opportunities. However, it’s essential to have things in place – such as your career roadmap, your resume, and LinkedIn profile – before your job search, as you never know when someone might offer you a great opportunity. [Listen from 28:55]

Sarah reveals that she initially started her work because she realized that boot camps were failing a lot of people on the “get hired” part of the promise.“The longer I’ve done this, now I realize the task of getting all your career stuff together never goes away,” Sarah tells Barry. You’ll always need career development, no matter what stage of your career you’re in. Even those who have been working in the field for 20 years or more still struggle with self-doubt and need help with their career development. [Listen from 33:00]

Designing structures and systems is crucial when building a community. Sarah gives examples of the types of rules and guidelines she put in place to make sure her community doesn’t become a “free-for-all”. She also talks about the coaching software she has built for her clients and how it allows her to identify problems before they become bigger issues, and make data-driven decisions. “One of the other big changes I had to design into my life, really, is recognizing that I can’t do it all,” Sarah comments. “I can’t reply to every social media message, I can’t reply to every email, I can’t go on every podcast. Setting those boundaries, I think, is so important, and it applies. …Because if you don’t create those boundaries, it leads to burnout, and you start seeing it seep into other areas.” [Listen from 33:55]

Looking Ahead

Sarah’s new podcast, Career Strategy Podcast, is a strategic marketing move for her business. She plans to repurpose the podcast content to create social media content and she has designed a system to make this happen. She also talks about her upcoming book with Rosenfeld, The Product of You, and how she plans to use the podcast interviews as content for the book. [Listen from 40:45]

A special message to listeners
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