Showing up as Your Unique Self: Emma Holland’s Job Search Success Story

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Find Your Dream Job, Bonus Episode 50:

Showing up as Your Unique Self: Emma Holland’s Job Search Success Story

Airdate: March 7, 2022

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life. 

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps you find a fulfilling career.

One of the best ways to get good at job hunting is to talk to people who do it well. 

That’s why once a month, I interview a Mac’s List reader who found a job they love. 

Our guest today is Emma Holland. She’s the national community and volunteer manager at StartOut. 

It’s a nonprofit that creates great business leaders by fostering LGBTQ+ entrepreneurs.

Emma Holland believes in the power of authenticity. In a recent story you can find on the Mac’s List website, Emma shares how she sought support from others and embraced her authentic self during her job search.

Emma, why do you love your job? 

Emma Holland:

I find the fact that I can show up every single day, not having to question with my colleagues how proud and how out I can be as an LGBTQ person, is one specific asset that I took for granted in some of my other avenues of employment. Because I currently work for an organization that focuses on empowering the LGBTQ community through what we do as a part of our mission. 

So much of who I am does not have to be called into question in how I do my work. I am expected to do my work regardless of how I identify, and that has not always been a luxury for me. 

Furthermore, how I contribute to our company’s mission aligns with the types of things that I am passionate about. What does it mean to build an authentic community? How do we make sure that we are leading with impact instead of just developmental opportunities or financial incentives? How can we champion the stories of the people around us and showcase their successes through the collaborative work that I do with my community? 

StartOut has created a space for me to not only be my authentic self with a group of passionate collaborators but also to celebrate other people who are on their own entrepreneurial journeys. 

Mac Prichard:

Well, tell us just a little more about the work at StartOut. You mentioned the mission; tell us more about that and what specifically you do on a day-to-day basis. 

Emma Holland:

What I have to say is that it changes frequently because we never know which programs are going to find values to different kinds of entrepreneurs in their businesses. 

We work as a dispersed team of remote employees for our nonprofit’s mission. The types of folks that we reach are all over the world. 

Right now, I manage ninety-five volunteers, who we call our programing board members, that hail from everywhere in the United States, but also Australia, Turkey, India, England, France, and so on. 

Being able to hear their perspectives, depending on what type of goal they’re working toward, changes, and the feedback that I receive from these folks is always very empowered and authentic. 

But our programs go beyond just what we do with our volunteer community, which is create and craft free educational events for other LGBTQ entrepreneurs, and help them in their search for access to capital.

But also one-to-one mentorship, where a StartOut founder is able to be paired with an expert to help them develop one of their business offerings, and we do that very, very carefully where everyone is hand-paired through a program manager who works with our unique experts to make sure that the founder gets what they need. 

We also have opportunities for access to capital, like I mentioned, in the form of demo days, where anyone has the opportunity to pitch in front of a series of investors. 

Community partnerships, where we work with like-minded organizations to showcase underrepresented founders. 

As well as our social media presence, where we profile and get to showcase off on a larger scale to over eighteen thousand members the successes of their fellow communities and potential offerings that they have by being a member of ours. 

Mac Prichard:

Terrific. Well, let’s talk about your job search, Emma. What was the biggest challenge you faced? 

Emma Holland:

The rejection portion was pretty consistent and something that I did not realize how much of a struggle on my own confidence would be as I was working. I am someone who was a career shifter, but I had been in various industries for nearly a decade, and yet the search itself and how frequently I was getting “thanks, but no thanks,” getting to that final interview and setting me up with a different candidate, actually getting a verbal offer while being told that my written offer would be coming, and then the company suddenly shut it down. 

There was a level of, am I really good enough to be doing this? Do I think more highly of myself than actually what my skills are? And the fact that rejection could actually sit with me and call into question my own skills and abilities, which had a proven track record, had plenty of references and recommendations, had data backing up what I was able to do. There’s still enough that can get under your skin. Wonder, am I good enough? Will I be good enough? Am I gonna find the next best thing for me? And will I be happy there? 

Mac Prichard:

I was impressed, in your article, how specific you were about the rejection that you experienced. You mentioned already that you were told to expect a written offer, and it never came because the company shut down. You also mentioned that you were ghosted by a recruiter. Nobody wants to have that experience. And you had multiple interviews with an employer, and then you didn’t get an offer. Talk about how you managed that rejection because, for many people, that would be discouraging, and they might give up or struggle for even months. What did you do to turn that around? 

Emma Holland:

It depended on the day, honestly, and I think that some of their rejections hit me harder than others and others inspired me to keep going. When I was ghosted by this recruiter, that was one of the first moments where I had to sit and think, wow. Am I really as attractive as a candidate as I perceive myself to be? Or is this a sign that I don’t really know what I’m talking about? 

What I decided to do as I started getting, you know, multiple rejections is actually work with a career coach. This is someone who I trusted, had been a former colleague, had been trained in various avenues of career coaching and strength finder, and different business caveats, who was able to sit down with me and kind of review my assets and to say, this is where I see you as a strong candidate for these types of roles. This is where you can make sure you tailor your application materials to really showcase this. This is how you can support types of answers that you might get in interviews and think of how you can talk about the actions you took and the task and the results that came through each of those samples.

That person helped me often cheer myself on when I felt like I wasn’t able to pick myself back up. So, I had someone on the outside who wasn’t dealing with the consistent rejection that I was navigating but was able to cheer me on and tell me, yes. You’ve got this. You know what you’re doing. You understand, based on your experience, that you know what you’re doing. Now, it’s just to find the right fit, not just any fit. 

She helped me understand also that everything that I am cannot be distilled down into a single interview question. Everything that I am cannot be simplified into a resume format that fits an applicant tracking system. Instead, I should be considering how I am showcasing only a part of what makes me a viable candidate but also a great collaborator and someone that they should be excited to work with because there’s only so much that they are able to see with me in the small section of our interviews. 

She also helped me understand that some of these are giving me a no because this is not the right fit for me. So, I need to consider the fact that it’s not that I am not good enough, but rather that this is not the opportunity that would serve me in the future. So, thank you. Next, we’re gonna go on to an opportunity where we fit better. 

What I can say is the most crushing was getting an offer from a team that I was so excited to work with, verbally, and an outreach from their team saying hi. We are so excited. We are looking forward to working with you. We can’t wait to have you on the team. We think you’re going to do great things. The manager that I had multiple interviews with, absolutely hit it off with. The director of the department I was really excited to work with had a proven track record of success in other Portland companies. 

And then to hear that surprise, to not only them but myself, that they were suddenly shutting down due to acquisition-related negotiation, and how that happens absolutely out of my control, absolutely out of their control. But I had expected to go into my next work week to say hello, I’m putting in my notice, and I’m so excited about this new opportunity. I had canceled other interviews actually because I was very confident in moving forward with this opportunity, except for one, that one being StartOut, where I landed now.  

Mac Prichard:

I’m curious, why did you cancel the interview with StartOut? And then, in hindsight, do you wish that you had not canceled the other appointments that were pending when you were waiting for that written offer? 

Emma Holland:

In hindsight, there was absolutely some, oh why did you do this? That was foolish. You didn’t have anything written down yet. You should wait to get this in writing, and I think, for future me, if I’m even in this situation again, that’s something that I’ve learned the hard way. 

I didn’t cancel my interview with StartOut because their mission seemed too good to be true, honestly, and I wanted to see. This was gonna be a conversation with their executive director, and something that I’ve learned working with startups, working in tech, and working in the nonprofit spaces, is that senior leadership is often a really interesting indicator of the culture of the organization and how they are driving their work forward. 

So, I’d had some really excellent conversations in my previous interviews with the COO, who’s now my boss, as well as with their senior program manager and their marketing manager to understand kind of the makeup of the team, the goals that they had. And it seemed truly, uniquely interesting, and for someone who identifies within the LGBTQ community, it seemed like a match made in heaven. 

But again, that imposter syndrome rejection was still lingering in the back of my mind, so I thought, you know, this is either too good to be true, but you just need to see what could potentially happen, and I’m very glad that I did. 

The conversation I had with that executive director, who is our executive director for the organization, I remember a question that I asked him was about, you know, what success story do, you know, are you the most proud of for the organization? Because I was very curious if he was aware as to how much work went into the programs beyond just his executive leadership. 

He not only gave me a great example, he then forwarded me a newsletter from that company saying, “Hey, this is based on our conversation. I thought you might like to see this.”

So, he was able to give an example of a founder who was really breaking the mold, had seen a lot of success, and then follow it up, completely unprompted, with an example of that conversation just because it happened to land in his inbox the same day, and I thought that that was pretty tremendous. That not only was the executive team aware as to what was being connected to, but they could follow up with actual examples. 

So, I could say some of it was instinct. You need to keep this because you just need to see what’s gonna happen. For future me, it is a do not cancel anything until you’ve signed your name to an offer document. 

Mac Prichard:

One thing that you did, that you write about in your article for Mac’s list is, create a schedule for your job search. Tell us about that schedule. What’d it look like? And how did it help you?

Emma Holland:

I’m someone who lives by my calendar, and I know that this is something I use in project management throughout my work I’ve done in the past. I figured, if this works for how I need to get inter department on projects across the line for what I do for work, I should be thinking about it the same way for my job search. 

So, there were certain days that I would set up each week to look for roles and apply for them. There were certain days that I set up each week to follow up with potential role leads or interviews that I had just had to make sure that I had sent, thank you. Is there anything else I can provide for you? Type of feedback. 

But I also had a day where I scheduled most of my interviews. Which meant I didn’t have to put all of my energy into being interview ready every day of the week. Instead, I would prep, and I knew that I’d have a bunch of calls back-to-back. Have plenty of energy for that day. Have my examples ready to be able to reflect on as well as notes about the organization that I needed to have ready. 

And so, at the end of each week on Friday, which is my interview day, and I would use that time just to prepare the questions that they had sent, some of the case studies, some of the technical assessments, depending on what organization I was interviewing with at the time, and it let me have a couple of days to rest in between starting on Monday looking for roles, by sending in potential applications and following up on leads. 

Mac Prichard:

I love the fact that you picked the day that you wanted to do interviews. Often, when candidates get calls from recruiters, they think, well, they just should take either the first available slot or whatever is available. But you took a different approach. How do you think that helped you?

Emma Holland:

For me, it was a moment to understand that I do have worth outside of just what this recruiter is looking for. My time is just as valuable as theirs, and I think that’s something that we’re very quick to let go of in the job space and just be, you know, amicable to whatever possibility comes our way. I knew that if I was to show up back-to-back after, you know, really tense meetings at work, to then an interview, that I wouldn’t be showing my best self.

So, being able to say thank you for submitting this availability. I actually am only available from this time to this time. Would that work for you? If not, happy to make amends and see if we can find something that works best for compromise.

Most of the time, each recruiter that I spoke to or potential hiring manager was very willing to make accommodations. They considered me a candidate they wanted to speak to. They understand that I was working full-time, and they were more than happy to make our ends meet so that it could be mutually beneficial. 

That was something that I found was not only appreciated. It was respected, and it didn’t come with any form of guilt or lingering push. If there was ever a time where I had to compromise, I understood that, yes, this happens. But the first thing that I can do is just ask and try to protect the time that I have, to know that I can show up as my best self and I can prepare for these types of days. 

I will say the luxury that I did have for myself is that I was looking at remote roles only. So, most of these recruiters that I was speaking to were very able to cater to those needs because we were going to be meeting over a Zoom platform anyway. 

Mac Prichard:

You work in technology, Emma, but you studied theatre in college, and you are very active in the arts as a performer. How did you persuade employers throughout your career and during your job search that your training and experience in the arts was transferable to the world of technology? 

Emma Holland:

I will never forget my first role in tech, and it totally came from a referral from someone who was actually in the cast that I was performing with. I think I was working as a content provider for a local e-learning company called Open Sesame. 

The manager I had at the time took a risk on me through this referral and allowed me to come into a role that was very much being established in real-time. As I wanted to take on more tasks, they would have me test things in different departments. 

So, they got to see how easy it was for me to navigate learning things quickly, requesting feedback, collaborating with a group of people, being able to present in front of a group of people in a way that would also request feedback live. This is something that I think the arts prepared me for because it is ruthless, often, in how it critiques its performers. You are putting so much of yourself on a stage for people to be viewed but also to be reviewed at the same time. You’re stepping into a character that might be unfamiliar, and you’re having to learn so much of the intricacy of what that person does or is in order to play it authentically. 

And something that I’ve learned with this space of being in technology is that you can learn it. It’s not just something that is inherently talented. It is a space that you can enter into and continue to upscale. I don’t think I will ever be a data scientist, I don’t think I will ever be a software engineer, but I did find that there are other roles that exist within technology for people like me that are community-based builders, that are project managers, that are operations managers, who like to see how things fit in the greater puzzle, how to get the right people in the room to provide the type of feedback that you need to push something forward, and to make sure that you fall on a timeline to execute something well so that you don’t miss a launch schedule. 

So much of that to me is reminiscent of the theatre rehearsal room and making sure that you’re scheduling the right people to be on stage at the right time to practice a certain thing before you put it in front of an audience. So, so much of my theatre training, my theatre profession, and how I have been working as a regional performer is very much mirrored within the technical spaces.

Of can, you collaborate well with others? Are you willing to try something new that might be outside of your comfort zone? Are you willing to learn something new that might not be what you signed up for initially, but that excites you? Are you willing to request feedback on a regular basis and not let that feedback crush you, but instead take it and work it to your favor to have a better end result? Whether that be with your product, whether that be in your role, and soon, maybe even asking for a raise.

You can find so many ways that you’ve become adaptable and also able to work with a diverse group of people that come from different thoughts and experiences, as well as talents and techniques, and find yourself molding with them to get to the results that you hoped to as a group. And so much of that is synonymous with what I experienced in theatre that it transferred very well to what can I learn? How can I learn it? Who do I need to learn from? 

And a lot of it also, I think, applies into the way I think of community and how you build those types of relationships. 

Mac Prichard:

Well, finally, Emma, what’s your number one job hunting tip? 

Emma Holland:

Oh, wow. Number one, for me, it would be to have someone that is your kind of accountability buddy. This could be someone who you actively work with. It could be a former colleague. It could be a friend that’s championing you on because there will be days that it just feels hard and impossible, and you will second guess yourself. Having someone outside of your experience who can remind you and ground you and help you recenter was so valuable for me. 

Working with that person to understand that my uniqueness cannot be summed up in an applicant tracking system. Instead, only part of myself can be shown here. So, how can I make sure I’m reaching out for when I need help? If I need a pep talk. I called this person regularly about negotiating my salary, about the offers that I was receiving, and how I can navigate which would be best for me. 

Having that person, whether it be a coach if you want to hire a career coach who’s really intimately aware of the landscape or that colleague who really understands you. A former manager was absolutely essential for me and helped me get through some of the imposter syndrome I was facing from rejections and also helped me feel empowered with my overall job search that, yes, I could do this, and I couldn’t wait to tell them when I had moved something forward.  

Mac Prichard:

Well, thank you for sharing your story, Emma. To learn more about Emma Holland’s job search, visit macslist.org/stories.  

And check out the Mac’s List website for dozens of other success stories. 

On the second Friday of every month, we add a new interview with a Mac’s List reader who has found a dream job. 

Go to macslist.org/stories.

In the meantime, thank you for listening to today’s bonus episode of Find Your Dream Job. 

This show is produced by Mac’s List. 

Susan Thornton-Hough schedules our guests and writes our newsletter. Lisa Kislingbury Anderson manages our social media.

Our sound engineer is Jeni Wren Stottrup. Ryan Morrison at Podfly Productions edits the show. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week. 

Rejection is a part of the job search that we don’t like to talk about. No matter who you are, it stings to be rejected, especially when you thought it was a perfect fit. How do you get past those initial feelings of not being good enough? On this bonus episode of Find Your Dream Job, Emma Holland and I discuss how she dealt with rejection and eventually found her dream job by refusing to give up. Emma also shares her experience using a career coach and how the support of this coach helped her overcome the obstacles she faced. Learn more about Emma’s career history below in this installment of our Success Stories series.


What do you do for a career? Who do you work for?

I am a community professional, which means I support a lot of an organization’s efforts to maintain and sustain satisfaction/retention with clientele, strategic partners, sponsors, and public brand trust. Community Managers engage audiences on a variety of outlets, including online forums, online events, Slack, small in-person groups, and more. Uniquely for StartOut, I also manage our volunteers via industry programming boards while directing community strategy for org growth, scale, and member retention.

I currently work for StartOut, the national nonprofit working to increase the number, diversity, and impact of LGBTQ+ founders. Our small team works to amplify our founders’ stories to ultimately drive the economic empowerment of our community. Please visit us: www.startout.org.

How long did it take you to find this job?

Somewhere between three and four months. I began applying while I was still a full-time employee for another organization.

How did you find your job? What resources did you use? What tool or tactic helped the most?

I was eager to find a new role. After working in a space that supported career switching for adult learners, I decided to put some of that strategy to use for myself. I applied for 4-6 roles a day, Monday through Friday, for three-ish months. I updated my resume formatting after researching applicant tracking systems. I created a new personal website. I sent messages to professionals on LinkedIn working in roles similar to those in which I was applying. I conducted at least one informational interview per week. I had a notification for LinkedIn to email me about remote roles posted with titles similar to mine within 24 hours, knowing I needed to catch them early.

I used LinkedIn, Idealist, Mac’s List, and (mostly) Slack to find opportunities and speak with hiring managers. Our local icon, Rick Turoczy, maintains an incredibly robust Slack group for the Portland Startup community, and the Out in Tech team has a vibrant group for LGBTQ+ folks in the job-search, providing career and resume advice. A dear friend and former colleague is a career coach based in Chicago. She gave me a ton of advice on my materials, my process, and how to negotiate. If you’re financially able, working with a coach can really be a game-changer!

What was the most difficult part of your job search? How did you overcome this challenge?

At one point, after months of rejection, I had a verbal offer from a Portland-founded finance company. My new manager had reached out, people were connecting with me on LinkedIn, and the recruiter told me at the end of the week they would send over the written offer. The very next week, only days later from my offer, news broke that their parent company intended to shut down all operations of this company by the end of the year. An hour after I caught the headline, I received an email letting me know they would not be able to move forward with my offer and had stopped hiring for their Portland operations. I was shocked and disappointed, having already canceled some of my following interviews – but thankfully held onto one that felt too good to be true. The following day, I had my final interview with StartOut’s Executive Director.

I don’t think I did 100% successfully overcome all the things constant rejection had me think about myself or my abilities. My current manager tells me regularly that my work is tremendous, shows me the data, and she’s telling me regularly that I should be proud (and not doubt myself). But there is some gaslighting that happens throughout a job-seeking process. Getting ghosted by a recruiter is terrible and makes you wonder if you’re actually worth someone’s time. Getting told after five rounds of interviews that they went with another candidate, on multiple occasions, really makes you wonder, “why am I not good enough?” After a couple of months, I decided to reach out to my community to share that I was struggling and the Program Director for Out in Tech became such a champion for me, offering intros and singing my praises. It was awesome knowing someone believed in me, and I felt stronger by asking for help in a trusted space.

What is the single best piece of advice you would offer other job-seekers?

Most of these systems are not designed for all the uniqueness you bring to the table, so don’t take everything to heart or you may doubt your worth. Also, some job postings list “requirements” but should be branded as “guidelines” – if you think you only have 70% of the experience they say they require, apply anyway! My main experience was in eLearning and EdTech, but I was interviewing with healthcare, finance, nonprofits, marketing agencies, and production companies. Practical moment: Make sure your resume shows your impact in your roles, with key data figures like “improved retention of clientele by __% in 6 months.” Also, look at the skills the listing is hiring for, then include the applicable ones (as comma-separated-values, not bullet points) in your resume!

Why do you love your job?

I am still amazed that as a nonprofit, my organization was willing to pay me more than the giant corporation I was working for, with better healthcare, all while supporting me being fully myself in a public role. My manager is incredible as a coach and collaborator. The team is intentionally diverse (this is the first org I’ve ever worked for with transgender representation on the Board of Directors) and our overall team focus is consistent: “what is our impact?” We are consistently centering on the experiences of our members and clientele. I’m trusted with autonomy and consistently have collaborators all across the organization supporting my work while helping me refine our strategy. I feel aligned with the mission and encouraged to be my authentic self – and I’m encouraged to take the time away I need to care for myself without guilt. It’s pretty remarkable how much better I sleep!