You’re ready to switch careers, maybe even career fields. You’ve got an idea of what you want to do but you aren’t sure where to start. On this bonus episode of Find Your Dream Job, Em Bookstein and I talk about how they overcame imposter syndrome in order to move into a new industry. Em also shares how informational interviews helped them get answers to the questions they had about a potential employer. Learn more about Em’s career history below in this installment of our Success Stories series.
Find Your Dream Job, Bonus Episode 48:
Fundraising for Social Justice: Em Bookstein’s Job Search Success Story
Airdate: January 3, 2022
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 Em Bookstein, the development coordinator at NextUp. It’s a nonprofit organization that amplifies the voice and leadership of diverse young people to achieve a more just and equitable Oregon.
Em Bookstein believes in the difference; that help from friends and colleagues can make.
Em, who uses they pronouns, decided to leave a career in software engineering for a job in nonprofit fundraising. Em says having support from important people in their life was vital in this career change.
In a story you can find on the Mac’s List website, Em also says informational interviews were their most useful job search tactic. The people they met not only gave useful insights into fundraising but also gave them confidence and informal mentorship.
Em, why do you love your job?
Yeah, I love my job because it’s something that I can contribute to that I believe in. So, NextUp is all about youth organizing. That is something near and dear to my heart. So, every day, when I’m doing any number of different things, whether it’s data uploads or talking to donors about why they should support us, it feels like I’m working in service of something I genuinely care about, and I guess in addition to that it really connects to something that has personally touched me. Before I joined NextUp, I was doing volunteer fundraising, and I always felt so excited to bring people in and help them feel connected to something larger than themselves, and I get to do that every day at my job. That’s what fundraising is all about.
Terrific, and why NextUp? You must’ve had your choices of nonprofit organizations; I know there are so many good ones out there. Was there one thing about it, in the organization’s mission, that attracted you?
Yeah, definitely. One thing that really stood out to me was the focus on youth organizing and training young people as organizers – supporting them in their own organizing journeys. That really resonated for me.
I got my start, I suppose, as an organizer with Resource Generation as a volunteer. Resource Generation is a nonprofit that mobilizes young people with class privilege and or wealth to redistribute those resources and redistribute power, and as a young person, I really have the benefit of being invested in as an organizer, and it is something that eventually, you know, transformed my personal life.
It has helped me work with people and become part of communities I never would have expected, and I see NextUp providing opportunities like that. Not with the same target audience, but providing opportunities like that for young people to be connected to each other. To fight for systems change, and to really develop their own leadership, and live the lives they want to lead in alignment with their values.
Well, let’s talk about your job search. You switch careers. You move from working in software engineering previously to nonprofit fundraising. How did you decide to make that switch?
Yeah, well, it definitely related to being involved in Resource Generation, the organization I just mentioned. But really, what it boiled down to was that each day at my job, I was more excited to do the work that I was taking on as a volunteer than I was to do the work that I was being assigned to and paid to do. And there is an incredible amount of privilege that I had and flexibility that I had in weaving in my volunteer work into my life. That’s definitely not accessible to everyone.
But yeah, I think that the real tipping point especially was, I took some time off of work to do some door-knocking and canvassing in Massachusetts. There was a ballot measure that would have stripped away legal protections for transgender people, and somebody who I really trusted was going to volunteer, and I followed them, and seeing the young people, young trans, and queer people, leading that campaign really touched me. And when I went back to work, I just found myself saying, why does any of this matter? And I really could not bring my full energy and attention to my job again after that. So, that’s really what prompted the switch. But it had been a process over time to reach that point.
So, you had that experience; you knew you wanted to make a change. How did you get focused on the exact change that you wanted to make? And clear about the exact work you wanted to do? And where you wanted to do it?
Yeah, it wasn’t obvious right away. I thought maybe I would become an organizer, somebody who’s more working with communities. Working with people to motivate them to take action and to develop their leadership, and I would say that fundraising is a form of organizing. But it wasn’t the first thing that crossed my mind. It wasn’t until I was really doing that self-examination looking at what strengths I could bring to the table – what could I even offer to a nonprofit that wanted to work with me – that the pattern of specifically fundraising became very clear.
My work with Resource Generation was all about organizing people to move money and elevate the work of others. My work with Social Justice Fund, a really incredible community foundation in the Pacific Northwest, was all about raising money for incredible grantee organizations who are moving the needle on collective liberation, racial justice, economic justice.
So, really, doing that examination and looking at what I had done and what I had clearly felt drawn to is what tipped me in the direction of specifically fundraising.
Tell us about the process you went through when you did that self-examination. Was this a process that perhaps a friend or colleague had shared with you? Is it something you designed on your own? How did you figure that out?
It was pretty self-designed. I think that one key piece of it, for me, was making two separate copies of a resume. Two separate, you know, job alerts, what do you even call them? Setting up different job alerts on websites. That was, kind of, what allowed me to explore and experiment with the idea of what work I wanted to take on.
And I do have to give credit to a class that I took long ago where they walked us through this design experiment called Odyssey. What was it called? Odyssey Path? Odyssey Quest? Of course, in this moment, the name is not coming to me. But, basically, it was about looking at the next five years of your life and saying, what are three completely distinct, different paths that I could do that would bring me personal satisfaction? And that’s an exercise that I frequently touch back to when I’m at a decision point or a fork in the road.
So, in this case, I just did two different paths, allowed them to flourish and be their own possibilities, and then really looked at the difference between those two. And I found myself resonating much more strongly with what I had laid out in a fundraiser resume than in an organizer resume.
I’m sure there’s so much more, of course, that people can do in terms of self-reflection and exploration. But that was a key part of my process.
As part of that process, did you talk to people who were doing nonprofit fundraising and people who were involved in the other option that you were exploring?
Yes, definitely. Yes, thank you for that question. That was also very key. I love to talk to other people about the decisions that they’ve made. It helps me understand and clarify my own decision-making. So I did reach out to nonprofit organizers, people who are more in the sort of policy advocacy direction, and I reached out to people who specifically do nonprofit fundraising, and, you know, I took them out to coffee. I asked them questions. I asked them for their stories, and that was incredibly helpful for me.
Why was that so helpful, Em, when you were talking with people over coffee, hearing their stories, and hearing about the decisions they made?
Yeah, I mean, I think that hearing about other people’s stories like that allowed me to sense what resonated the most for me. So, when I was listening, for example, to people talk about their fundraising work, or how they got into fundraising, or why they like it, or what its challenges are, I felt the most excited. I felt the most sense of possibility. I felt the most sense of potential. And some of that did come from, you know, previous self-examination around, what are my strengths? What can I offer strategically? Especially as a white class privileged person with the experiences that I have. Where could I position myself strategically?
And so, coming into the interview with that mentality of wanting to position myself strategically and somewhere that would really suit me. Listening for that in those informational interviews was really helpful.
What advice would you have for someone who might be reluctant to approach others for informational interviews and ask them for advice?
Yeah, well, not to get technical, but it would depend why they would find it hard. But I imagine that one thing that people might be afraid of is fear of burdening someone, or fear of intruding, or asking too much. And I would say to that, people seem to love to tell their stories. Every time that I’ve reached out for mentorship, or advice, or input, I’ve found that people are really willing. Maybe they remember that somebody offered that to them, or they’re excited to pay it forward, or they do just really want to share what wisdom they’ve gained from their own life experience. But I find that people seem very excited to talk, and if they’re not, it’s simply because they don’t have time. So, my encouragement to anyone who’s thinking about doing more informational interviews, just reach out. Somebody might be really thrilled at this opportunity to pass on their knowledge to you.
Once you were clear that you wanted to pursue a position in nonprofit fundraising, what was the biggest challenge in making that switch from being a software engineer to a nonprofit fundraiser?
Yeah, I think the biggest challenge was worrying that I didn’t have what it took or that nobody should hire me. I think there’s a sort of blend of healthy self-doubt mixed in with some imposter syndrome there. But the healthy self-doubt part is just, you know, what am I bringing? What are the skills that I have? Where do I stand to grow? The imposter syndrome part is, no one will ever hire me because I can’t do this. But yeah, those were sort of two internalized or mental challenges.
And how did you overcome them, Em?
I’m so glad you asked. It was really thanks to people around me who were encouraging me and who could reflect back to me what they saw of me. You know, I think, sometimes, it’s really easy to internalize a really warped view of yourself. I mean, perhaps some of it is warranted, but a lot of it is not.
Just thinking for myself, you know, I think it was right to question whether stepping into nonprofit fundraising would be right for me. But in terms of the reflection that I got from the people around me, people who had organized with me, people who I had fundraised, people who had seen me really come alive and feel passionate about that work; they were all alike, “No, you definitely can do this because you have done it, and you’re clearly drawn to it. So, we’re behind you all the way.”
And I’m thinking specifically, actually, of my manager, my manager who worked with me when I was a software engineer. She really believed in me; she supported me to leave my job. There was a friend of mine who was an organizer for ten years who also was a big advocate for me and a cheerleader for me.
And then people I had organized with. So, having that community of support was what got me through it.
You learned about the job at NextUp, and you applied. What concerns did you have to address when you met with your future employer? What kind of questions did they raise about you making the career switch? And how did you address them?
Yeah, good question. Just for clarification, do you mean what questions did I have for them or that they had for me?
Uh, I think both because – I’m so glad you brought that up because it is a two-way street. I think, when you apply for a job, you’re interviewing an employer as well as being interviewed. It’s a conversation. So, thank you for making that point.
Yeah, definitely. Well, the questions that they asked me – I mean, a lot of it was about wanting to hear my experience with fundraising. They also really wanted to understand my racial equity analysis and what kind of perspective I would bring to this job since it is – at the time, actually, it was an entry-level role as a part-time development associate. So, it was as important to them to know what I was bringing in terms of my analysis and perspective as it was to hear about my experience.
And I’m sorry if that’s not very specific. I don’t remember their exact interview questions, other than a question about, you know, connecting NextUp’s work with the larger picture of racial equity in Oregon and in the United States.
And as for my own questions for them, I think I was very concerned about what kind of support would be available and whether it was a team that was all very individualistic and sort of isolated or a team that worked together.
And I remember asking in the interview about goals for the organization and whether it was all on one person to meet those goals or if it was a more collective sense of ownership. And that was important to me to ask because I believe, and maybe this actually came from the tech world even; there was this saying that, if a newbie software engineer made a mistake that ended up in production, aka, live on a website, that that was a collective failure, not the individual person’s mistake.
And I feel like that does actually really resonate with my values, which is that failures and successes are collective. They’re not individual. And so, I did want to know that about a future employer. Do they see us as a team who collectively works for goals or as a group of individuals doing our own tasks? So, that was important to me to ask.
What was the key to your success in your job search?
Well, I would say informational interviews. Not to be a broken record, but you know, I think being able to find the job post on Mac’s List was really huge, obviously. I did not know about it, but once I saw that posting, I actually realized that I knew someone who was on the board at the time. And I reached out to her and asked if we could have coffee, heard more about NextUp, really felt confident that the work aligned with my values, felt sure that I could bring something to that space; at least more confident, we’ll say, not sure.
But yeah, it was really helpful to talk with her and hear her perspective on the organization, and that gave me a lot more confidence in applying. It helped me feel some familiarity with the organization by the time I was in the interview. Yeah, so I can’t stress enough how important that connection was as far as my job search.
Well, finally, Em, what’s your number one job hunting tip?
Informational interviews! Yeah, I definitely understand if it’s not as easily accessible. It does require reaching out to people and making time for that one-on-one conversation, but it’s honestly my go-to advice any time a friend is talking about switching careers, switching jobs. Yeah, I hope that people can reach out, find the questions they’re most wanting to know, and be able to ask them directly and get that connection, get that feedback. That’s my number one tip.
Well, thank you for sharing your story, Em. To learn more about Em Bookstein’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.
This is Mac Prichard. See you soon.