Jamie overcame UX job search struggles & got hired as a Sr Product Designer

Sarah Doody [00:00:00]: Hey there. I’m Sarah Doody, host of the Career Strategy Podcast. Many professionals are seeking more impact, flexibility, growth, and let’s face it, getting paid what they’re worth. But how do you unlock this in your career? It starts with strategy. I’m taking you behind the scenes of what’s working for my career coaching clients. You’ll hear strategies and actionable, yet sometimes against the grain, advice for how you can be the CEO of your career and stop dreading Mondays. Ready to level up your career? Let’s get after it. Thank you all for joining us.

Sarah Doody [00:00:40]: This is our June open house and q and a with alumni of career strategy lab. So if you’re here, you’re probably curious about career strategy lab. You maybe are interested, wanna hear stories from people who recently got hired. So if that’s you, you’re in the right place. So first of all, we have Jamie, currently lives in Canada. Jamie got hired as a senior product designer at a software company, and Jamie is from living close to Ottawa, Canada, close to where I am from actually or grew up. So let’s dive into kind of our initial round of questions here. I would love for each of you to introduce yourselves and tell us, like, a little bit about what you’re doing now and what you were doing kinda before you joined Career Strategy Labs.

Jamie O’Leary [00:01:34]: Sure. Originally, I’m from Ireland. Hopefully, my accent hasn’t fully disappeared, but I’m based in No.

Sarah Doody [00:01:40]: I’m still there.

Jamie O’Leary [00:01:41]: That’s good. That’s good. I’m based in Canada now in Ottawa, as Sarah has said. In terms of my journey, I’ve been in design for probably 12 years at this point. Originally, a graphic designer, then switching into tech. And like Jaden, I had around 5 to 6 years experience in tech before I got laid off during that period when so many companies were were letting go of designers. And I was still quite confident that I would be able to get a job after that layoff. I had a decent portfolio, and I felt I knew how to put my resume together and articulate my experience.

Jamie O’Leary [00:02:20]: But given the competition and given the environment at the time, it just proved to be extremely challenging for me to to get work. And I was applying for 100 and 100 of jobs, tens of jobs every day, and I was getting some success. I was getting interviews, and there was some some encouraging signs, but I just couldn’t seal the deal. I couldn’t get that job. I couldn’t land it. So, originally, I’d worked with an individual career coach who who helped me out to a certain degree. It wasn’t the exact fit I was looking for, and what I thought I was really missing was the the community you get from career strategy lab, working with a team of other designers and working with the mentors, and that’s such an important part of career strategy lab, the support you get. That was what I felt was missing.

Jamie O’Leary [00:03:13]: I was nervous because I had already spent quite a bit of money on the career coach I originally was working with. And, obviously, being unemployed, it’s a big financial commitment. But in the in the back of my mind, it’s it’s always a good a good opportunity to invest in yourself. It’s never wasted money. So I took the the chance in career strategy lab just being aware of Sarah from from her thought leadership work, seeing her post on LinkedIn and on our podcast. And I was I was confident that I was gonna get a good experience. And and working through the the time I spent those 2 or 3 months I had with Career Strategy Lab, obviously, honestly, it really it really reset me going from a a mindset of being lacking in confidence and feeling defeated. And I’ve always struggled with impostor syndrome as a designer.

Jamie O’Leary [00:04:08]: So just having that support of the team and having such a solid set of frameworks and all of the materials so well organized, it it really helps set me straight. And right now, I’m working as a senior growth designer with a a team called Contact Monkey. It’s a b to b organization, focused on email marketing.

Sarah Doody [00:04:30]: I I really appreciate that you hit on, you know, this this element of community inside career strategy lab, and then it really helped helped you with, as you said, that imposter syndrome and and confidence and things like that. And I’m wondering, you know, for all of you, are there kind of overarching mindset shifts that stood out, you know, unique to you during your time in career strategy lab, similar to what to what Jamie said, or maybe Jamie you have more. So I’ll kinda open it up to see who who else might wanna share on that topic.

Jamie O’Leary [00:05:06]: Yeah. I can speak to my own mindset shift. And then certainly just realizing that there are a lot of other designers in the same situation as me. Being in a job search on your own is just so challenging, and it’s it’s really hard to keep motivated and keep positive when you’re getting those rejections every day. So my first mindset shift was that, you know, I’m not alone, and there’s a lot of people in the same boat as me and a lot of designers who are talented but still just can’t find the work. And my second mind shift was that looking at my materials and my past experience, I’m actually I am a solid designer. I’m good at what I do despite the fact that I’ve got let go and have had challenges in my career. I’ve got lots of wins.

Jamie O’Leary [00:05:56]: I’m working through the career road map materials around assessing my previous career positives and some of my failures and helping to reframe those started to put me in a positive mindset and really put me in a a solid frame of my mind going to interviews whereas sometimes going to interviews because you’ve been rejected so many times, it’s almost, you’re almost going through it with a mindset of being defeated before it’s even happened because your mindset is negative, and you may not even fully realize it. But taking the time to step back and really assess your previous career and what’s gone right and also what’s gone wrong really helped me reframe that reframe things.

Sarah Doody [00:06:41]: Yeah. I did. Before anyone else speaks, I just wanna, like, double highlight that because I think this is one of the things we hear quite quite often where people doubt their skills, doubt their experience, as you said. And, you know, the feedback we often hear from people is that the very act of joining Career Strategy Lab, and then thinking more deeply about my resume, my LinkedIn, my portfolio, and the projects I previously worked on, and making sure that I really recognize my contributions and my skills on those projects. That’s really where the transformation is. Because I think many of you don’t think deeply enough about what you’ve done in the past. And you just kind of think, oh, well, I was responsible for research, or I made a design system, or I, you know, was the interaction designer or something. But you don’t really dig into the nitty gritty of no, what did you actually do? And I think what you’re saying is, you know, that process of thinking through what you did previously was a big part of realizing, no.

Sarah Doody [00:07:54]: Wait. I really am awesome at what I do, and I just need to figure out how to communicate that more more effectively.

Jamie O’Leary [00:08:01]: It is so hard to do that on your own Oh. When you’re, you know, on your own in your office and trying to motivate yourself to to take that time to write the case study and to think back in your career. You really do need the the frameworks and the support of the mentors and the group of other designers. It really helps facilitate that process.

Sarah Doody [00:08:24]: So if if you forget or or don’t know, career strategy lab is divided up into these 5 sprints, for example, resume, portfolio, job search interviews, but the first one is your career roadmap, and it’s like a product roadmap for your career. And so one of the activities in there is kind of identifying people that you are inspired by or that you wanna emulate because oftentimes, you know, when you do that, it helps you get clarity on on the future of your career. So I’m curious, you know, thinking back to that first sprint, the career road map sprint, does anything stand out, you know, in hindsight? I know it may have been a while ago, but had had you ever done anything like that before? Or what do you think the impact of that sprint was on, you know, this whole journey?

Jamie O’Leary [00:09:16]: Yeah. I can I can speak to that? Certainly for me, and I’ve I’ve spoken to this a little bit previously, but it was really about taking the time to look through my previous career experiences and just really appreciate the depth of the successes I’ve made and overcoming the challenges I’ve had. And that was really important in terms of, like, building that confidence and getting over that imposter syndrome. Looking at the past 12 months, even if it hasn’t been the best 12 months I’ve been looking for work, I’ve still achieved a lot. You know, I’ve been working really hard. I’m committed to this job search and thinking about all I’ve learned. Those were some really positive things that I took away from it. Reaching out to my past colleagues as well and hearing about all the positive things that they had to say about working with me.

Jamie O’Leary [00:10:08]: And it was interesting. There were some clear themes that came back from everyone I spoke to around my teamwork and my ability to collaborate and UI skills, those were some things that stood out. So it was really encouraging for me to get that feedback and helped me build that confidence as I move through the rest of the the CSL course.

Sarah Doody [00:10:32]: Do any of the other sprints jump out to you? You know, like, this one was really powerful or this one really was a game changer for me.

Jamie O’Leary [00:10:38]: Certainly, the case study sprint was super impactful for me. Taking the time to go back and really think about exactly what I did in each case study, go into the real level of detail and nitty gritty that was required to be able to tell that story really well was as painful as it was for me. It was so important, and it just allowed me to have a level of detail in my case study and my story that not a lot of other designers have when they speak about their work. And I even had quite a few interviewers reach out to me and say that was one of the best case studies they’ve they’ve been presented with. Maybe they were humoring me. I’m not sure, but I’ll take it. And also the the networking, learning how to really effectively apply for a job, not just sending out your resume on job sites and applying for jobs over LinkedIn, taking the time to connect with people on LinkedIn, foster relationships, comment on their posts, start conversations, and just build rapport so that people have you in their mind. When they’re looking through those resumes.

Jamie O’Leary [00:11:48]: They already have a little bit of an idea of who you are, and that just helps you stand out from the crowd. Trying to be intentional about how you message people and not just sending a generic message, taking the time to read the job description, read their profile, and crafting a an intentional message really went a long way to helping me land quite a few interviews.

Sarah Doody [00:12:11]: And for the record, I’m going to guess that feedback that you received about your portfolio being, you know, so amazing after the interviews, I’d wager I guess they were telling the truth because we hear that from so many people. Like, they come back to the community and they say, oh my gosh. I just went to an interview. And, you know, one person said the people in the interview were taking notes for their portfolios so they could fix their portfolios after the interview. And I just thought that was really powerful. One question. It’s great for the for the group we have here today. You know, one of the questions we are asked quite often is, like, will career career strategy lab work for me if I’m outside of the United States? And, Jamie, will give you Ireland slash Canada.

Sarah Doody [00:12:56]: Kind of before I give my take on that, do you have thoughts on, like, the the relevancy of career strat job and and if, you know, being in a different country mattered, if anything?

Jamie O’Leary [00:13:08]: The details, the the the frameworks, and the course is so well structured. Everything is available, neatly organized videos. It’s housed in teachable online. The everything is easily accessible. And as a detail oriented person, which I am, it was just so easy to navigate through everything. So whether you’re in North America or elsewhere, it’s really, really very well organized. And I don’t think you’ll get that level of detail from another course, no matter where it’s located in the in the globe.

Sarah Doody [00:13:46]: Alright. I’m gonna I’m gonna pose one last question. So the last question I have is if you could give someone one piece of advice, let’s imagine they’ve joined career strategy job or maybe they’re on the fence. So decide, you know, which which way to answer this. But if they just joined, what’s one tip you would give them? Or if they’re on the fence, what would you say to them?

Jamie O’Leary [00:14:08]: And you

Sarah Doody [00:14:09]: could you could answer both if you want to also.

Jamie O’Leary [00:14:12]: In terms of if you want if you’re on the fence, I would say go with the option that’s gonna give you the best result. Even if there are other courses out there that maybe they seem comparable, maybe they’re a little less pricey, or maybe there’s more cost effective option, go with the option that’s gonna give you the best results and has the most detail, the best community, the best mentors. Because for me, I as I said previously, I did work with another career coach before I joined CSL. I thought this would work for me because, you know, I’m already an experienced designer. I have a portfolio. I just need someone to give me a small little bit of an extra push to help get that job. But in the environment right now where things are so challenging, you really need the best help to get yourself that role. So if you’re on the fence, I would say commit to the best option, which is which is CSL In terms of how best to utilize the course, definitely the community.

Jamie O’Leary [00:15:18]: So don’t be shy about posting on the community chat board on circle. Be sure to attend all of the coaching sessions and leverage your mentors, leverage your community, use the opportunity to share your challenges, be vulnerable. I spoke about my challenges with imposter syndrome and also mental health during my journey, and it was super helpful to get that feedback from and empathy from the wider team and to understand that there’s lots of other designers in in a similar similar spot as me. So I would say just leveraging that community is really the most important and powerful aspect of CSO.

Sarah Doody [00:15:59]: Well, thank you for sharing, like, these tips. We’ll talk to you soon. Thanks for listening to the Career Strategy Podcast. Make sure to follow me, Sarah Doody, on Twitter, Instagram, YouTube, or LinkedIn. If anything in today’s episode resonated with you, I’d love to hear about it. Tag me on social media or send me a DM. And lastly, if you found this episode helpful, I’d really appreciate it if you could share it with a friend or give us a quick rating on Spotify or review on Apple Podcasts. Catch you later.