The Career Story and Advice You Need to Hear Before Starting a Career in HR

Pauline HR image

Pauline Bailey, Director of Human Resources at Punahou School, answers the phone and I immediately understand how she’s excelled in the field. There’s a laugh in her voice that’s infectious and I find myself grinning into the receiver on my end.

Even though this career seems like the most natural fit for her personality, I am eager to hear about her journey into this profession.

I am totally unprepared for the story that follows. Pauline’s path is filled with uncertainty, recovery, and enough “leaning in” to knock the socks off Sheryl Sandberg.

Here’s the unexpected journey of one woman and the reasoning behind why she recommends students try other things before starting a career in HR.

Kellen McKillop: Since we are a site for students and recent graduates, I thought that you could tell me about your career journey and how you found yourself in the field of Human Resources.

Pauline Bailey: Well, I’m really old so it [my career journey] may be different from yours these days… [she laughs] but I think part of the difficulty for me, even though I went to Punahou School and had access to a great education, was that we had no college counseling and careers for women were either a teacher or a homemaker. Those were really our choices.

So, I went away to a college that wasn’t necessarily a good fit for me. But I certainly learned a lot in terms of being a true minority for the first time. In Hawai’i I really wasn’t. At Punahou I was a minority (we didn’t have a lot of Asians in those days) but certainly going away to the mainland I truly was a minority. I think that was potentially a precursor to me trying to understand the way people work.

I was an English Lit major. So again, I was at a place where I didn’t have any idea of what my career could be.

I moved to Los Angeles after I graduated and I actually ended up working part-time at UCLA and part-time as a waitress, singer, bartender. I was really just experiencing life but because I was an Asian and “supposed to become something more,” I decided to apply to graduate school in secondary education. I was supposed to become a teacher (remember that was my career option).

So I did that [graduate school] for a while and also continued to work at UCLA in public health, pursuing primarily admissions work.

It was a people intensive business because I’d interview applicants and review all those kinds of things (again, a precursor in a way). You know, applying to college is not all that different from applying to a job. You’ve got to research the employer or college, you’ve got to write your cover letter or essay, and you’ve got to figure out whether you’ll be a good fit.

So I did that for a while and I danced. I had always been a dancer—all through Punahou and all through college.

Then what happened was that I got into a really bad car accident.

KM: Oh, you did?!

PB: Yes, I was in the hospital for a little while and I couldn’t walk for about a year. I didn’t have insurance coverage while I was in the hospital. This was a catastrophe! I didn’t really have a way to pay for things so I basically had to go on welfare. Luckily I was able to get back to work at UCLA, but again, it wasn’t retroactive benefits coverage so I had to pay for all that.

So there I was, experiencing more of life’s hardships than I thought I would, and something that I loved (dance) had been robbed from me. I decided that I wasn’t going to take anything for granted anymore, so I quit graduate school and decided to see what life had for me.

For a year I really worked hard to rehab. I kept saying, ‘I’m gonna be able to dance again. I want to be able to dance again!’ I had kind of shattered my hip, so it was a little bit iffy.

There’s a story behind this. I’ll get to it soon.

So, I was taking dance classes and of course in LA it’s pretty competitive if you want to be any good. A friend of mine that I was taking dance with wanted to try out for a show. She wanted me to go with her because it really is cutthroat and I said, ‘Sure. I have nothing to lose. I’m just trying to prove to myself that I can dance.’

So I went with her to this audition and they ended up calling me and saying that I got the job! The job was in Las Vegas for the Tropicana hotel, the Folies Bergere show (which was one of the big acts). It was a weekend and they basically said, ‘If you want this job, we’ll see you in Las Vegas next week at 10:30.’

I said, ‘What the heck? I’m just gonna go!’

Everything was against me. My parents were completely mortified that I wasn’t going to be in graduate school and that I wasn’t working toward a ‘profession,’ but again, part of being in a near death experience was that I needed to go out. I needed to travel. I needed to figure out more about the world and myself.

I ended up dancing professionally for about three years and traveled the world. It was an amazing experience and I probably learned more about people and life itself than I would ever have in graduate school or working somewhere in a traditional job. It gave me a lot. I was really shy, but being in a show allowed me to transform myself and I got to know a lot about hemming myself around people.

But, I still felt the need to legitimize myself, so I went back to the mainland. I lived in the Haight Ashbury area and worked at UCSF because of my writing skills (English Lit, remember?).

I started working in a research department called Human Development and Aging. It was a multi-disciplinary program within the school of medicine. I was right up on the hill, drinking my coffee, and taking the N-Judah to town. I just loved it. I worked with these amazing people as a Program Editor.

KM: And what is a Program Editor?

PB: They [the Human Development and Aging department] wrote a lot of research papers, publications, and books, and so basically I edited most of their publications. I helped proof a lot of things. I did research. Interestingly again, in the field of Human Development. There’s a pattern here that I wasn’t quite aware of at the time, but there was definitely a pattern.

Fast forward and I decide to move home [Hawai’i]. I still felt that I wasn’t legitimate in the eyes of my parents and peers. I’d done my thing and it was like, ‘When is Pauline gonna settle down and become a real person?’ That was the pressure of being in an Asian family, I think, where my brothers and sisters were doctors, lawyers, and corporate heads.

So I said, ‘Okay, I’m gonna go to law school.’

But instead of going straight to law school, I decided to work at a law firm. [Editor’s note—we totally recommend this. See our article on deciding whether law school is right for you to find out why.]

I worked at a law firm and I started out as a secretary. Quickly what happened was I became, I think, different from any secretary that I’d ever known. I started doing a lot of paralegal work. I managed people’s accounts, real property. I was a concierge. I arranged for things like if the Taipan of Hong Kong was going to London, and he had to come in for a conference, I would call heads of companies and try to find private jets… it really was a very, very fascinating job and I had to be really creative about all this stuff.

I got to meet a lot of people who were among the world elite in this job even though I was just an executive secretary. I also managed the office in terms of hiring all the secretaries and paralegals and establishing the data systems. I was sort of a jack-of-all-trades. If there was a job to be done, I’d just sort of do it.

KM: Did you just pick… I mean, establishing all the data systems… did you just pick that up on the job?

PB: Yeah, everything was on the job. Actually, a really good way to learn, I think. For some reason the partners at the firm really respected my ability to do that.

In the end, I never did go to law school.

Then our company merged with Carlsmith, which is a big law firm here, and I decided that I didn’t want to do it anymore. I was pigeonholed in the larger law firm in a way that I hadn’t been in the smaller firm. So I said, ‘Well, what haven’t I tried?’ And what I hadn’t tried was corporate.

So I went into corporate and I started working at Pacific Resources (PRI) which also had a gas company, so it was an energy company. I just applied for a job there and somebody liked me and created a job that was called Manager of Administrative Services (or something like that).

KM: Wow, they made it for you?

PB: Yeah, they made it for me, but I wasn’t sure if it was a His Girl Friday type of position. But I was just like, ‘What the heck? I’ll give it a shot.’ I had an office on the executive floor and what it really did was allow me to get my feet wet in identifying the needs of a company.

It [PRI] was going through a lot of merger and acquisition activity so everybody was shuffling around and bosses and CEOs were being terminated right and left. I probably had four CEOs in five years. We had project teams that had to, you know, do everything, so we’d bring cross-functional teams together to look at business development.

I got to participate in all these committees and things like that, all while trying to prove myself to the newest CEO. Because it was a merger and acquisition time, we also had to merge company cultures. It became a multinational company. It was purchased by one of the largest publicly held companies. I learned a lot about Human Resources just from being in the place I was at the time.

I was on the fast track there and again, for a woman at the time in the oil industry, it wasn’t easy. I was also, at the time, thinking about having kids; the clock was ticking. Then, I was hiding my pregnancy. Because of that, I got involved in some other HR stuff as well.

I created one of the first family-friendly policies in the company and basically made the case that we were supporting men who did armed services work or were in the national guard and all their leaves, but we weren’t supporting women who were giving birth to the people who were going to later on serve the country. I was a little bit of an activist in that way, you know, creating a lot of different kinds of things around benefits for working women.

I was on the high-potential list. My job expanded. I became the Facility Manager and we had offices all over the place. I was traveling a lot, purchasing facilities, building facilities, and leasing facilities. Then, I also became the Corporate Purchasing Manager so I was buying cars and fleets and all that kind of stuff. So I was doing the corporate track in a man’s world (and often in Texas and Australia, which were very male dominated). The reason I say this is because I learned a lot about humanity. I was really curious about it and can you imagine this local girl right in middle of all this stuff?

But it still wasn’t who I really was. Okay, Kellen? It still wasn’t who I was. I did well at it and I loved every minute of it, even the most challenging times—and there were challenging times where I was working 24/7 and everyone was getting laid off all the time. It was really crazy and there was a lot of back-biting and a lot of people under the bunker and stuff like that.

But then, I had my second child and okay, with my second child I was back to work the next day. You couldn’t skip a beat. So I was looking for childcare options and the unemployment rate was really, really low in Hawai’i. You know, it was right before the Persian Gulf War and the economy was getting a little crazy and everyone had to work two jobs. I was just sitting there going, ‘I can’t find decent childcare and I’m not even making enough to pay what it would be.’

I started looking at options and I found this place that took care of infants and toddlers but it was going to close because it had run out of start-up funding. So I started working on it as a non-profit. Silly me, I decided to rally around it as one of the only options for working women downtown and I said, ‘Okay, we gotta save it!’

Right around that time I’d done all the stuff in administration, right? I’d done purchasing, facility management, database deployment, all those kinds of things. My bosses said the last thing I needed to really round out my administration experience was human resources.

I actually got to skip a lot. They immediately made me the Vice President of compensation and benefits (or something like that) and so I was in that job for about two months. I was still doing the facilities too and I was in Washington DC closing out a facility when I said, ‘You know what? I need to do this non-profit. I can’t keep writing grant applications at midnight. It [the non-profit] needs our support.’ We were just barely able to make the payroll every month and I said it needs my (or somebody’s) full-time attention.

I went to my company and asked for a leave of absence, a three-month leave of absence. They turned me down. HR turned me down. They were like, ‘We’ve just been acquired. We can’t do this… you might as well just quit.’

So I thought about it and I said, ‘Okay, I guess I’m gonna quit.’

I gave my, I think, three weeks’ notice and it was really hard for me because I didn’t think I had enough money to last me more than three months. But I did it anyway and then two days later the CEO calls me and he wants to know why I’m doing this. I was on the high-potential track. Why would I give it up?

I told him, ‘I don’t want to go to my grave and think that I walked away from something that is desperately needed for working women and men.’

He said, ‘Okay, well I think you deserve to succeed.’

Two days later we went on a drive around the island and just talked and talked and talked. He ended up giving me a year’s leave with pay to work on my non-profit and he gave me a corner office on the top floor. He gave me a bank of computers that I could use to start my business and because of the people that I met, I was able to get started. People gave me their club memberships for a year to do my fundraising. I got advertising agencies to do pro bono work. I had attorneys do all pro bono articles and everything else. People just came out of the woodwork.

KM: Wow.

PB: This is where I actually found out who I was. I realized that I always believed (and I think this has been my motto for a long time—before social entrepreneurs became the fad) that altruism and the bottom line do not have to be mutually exclusive. I found my calling in that.

I needed to help others, but needed to do it in a way that could be economically sustainable. You don’t have to give up who you are or your position in life to be able to do it. So I ran this non-profit business for a year and then went back to work for my former company. [When I returned] the company said, ‘Okay, we have two positions for you. One is the VP of Business Development for the gas company and the other one is VP of Human Resources.’

I really liked marketing and business development but I didn’t get excited about selling gas.

So I said, ‘Okay, I’ll do HR.’

I had more experience [in HR] than I realized. I’d run my own business. I’d had to fire people before. I’d managed people before. I’d had HR turn me down before. (And had been without benefits before). I had been a customer of HR for both bad and good. I said, ‘Okay, maybe it’s good that I have this experience because I can now put my own frame on it, right?’

That’s how I got into HR.

I think the life motto is don’t pigeon that hole for yourself. I mean, really, do NOT pigeonhole yourself. EVERYTHING you learn is useful.

For HR, you have so much more credibility if you have life experience. If you want to go into this field and you don’t think you’re going to go outside and run your own business, learn to fire people, and earn your own money, you’re going to have that much harder of a time getting taken seriously by the people you’re supposed to consult to.

KM: That was the only other question I had for you. Just about students who want to get started in this field…

PR: It doesn’t mean that you can’t do that. For those people who go into a track, and say they go into HR, it really is a very multidisciplinary field. You know, there’s back of office, huge amounts of compliance, huge amounts of IT, huge amounts of data. Now that we have the access to cloud services, you can do big data. The need for really good problem-solvers and people who can build databases around human capital is huge. It’s a fabulous career in and of itself.

You can have that track. I still suggest, though, getting out and learning about the end users. If you think you’re gonna go into HR just because you like people, that’s not nearly enough!

I think, again, it’s really good to read as much as you can, certainly take classes if you can, but you don’t need to. Like me, I never took any classes but I do think psychology and sociology and potentially anthropology are VERY important because they’re cultural. Understanding global cultures is very important.

With the field, you get a lot of range. You’ve got to have math, writing, critical problem-solving. You’ve got to understand technology, social media, and you certainly have to understand communications and culture. You have to understand organizational development and then you have to understand negotiation and conflict resolution.

So in your full day, you have a whole gamut of things (which I love). People who like to be pigeonholed probably shouldn’t come into this position. If you’re going to go right into HR, and you’re gonna get your MBA in HR at night, and work and intern at a place, those are all really good experiences.

Go and work at an outsourcing firm that does all the management of small businesses. Go and work in a firm that does recruiting or college recruiting or whatever else. Do that but WHENEVER YOU CAN, find a place where you can work on an assignment cross-functionally with some other department in there.

If you want to be good at compensation, no one will ever believe you unless you are able to sit in the shoes of the person you’re determining the compensation for. You’ve gotta do that hard work if you’re going to be really effective.

By the way, that’s what makes the job MORE fun.

Also, keep on top of tech. Don’t just keep doing things the way that they’ve always been done.

I can say this about almost any career: the half life of content is a nano-second. It is changing all the time. We don’t have to know all the answers. In fact, if you think you know all the answers, no, you’re wrong. Just be able to seek answers.

You also can’t be purely quantitative in HR because you are not in control. Humans are a messy business. There are a lot of messy problems (which I think are very fun and very challenging)!

I have a Kuan Yin, actually two Kuan Yins, sitting in my office. A Kuan Yin is a Bodhisattva who hears all the cries of the world. Empathy is extremely important. So you need the well-developed right brain and left brain. A left and right that can talk to each other, that can easily merge logic and data with feelings and user understanding, the context of people’s lives.

I think that will make for a really, really great person in this career in a leadership position (if that’s what you want). If you want a narrow position in HR, there are many, but to be truly effective and to really make the HUMAN part of HR come alive, I think you really want to be able to try all the jobs. Try ‘em all out and know that there is no substitute for the experience you get working for people.


Homework time! Pauline says that she thinks it’s possible to get your Master’s and go straight into HR, but that you should complement your education with real-life experiences. Consider spending a year or semester abroad. Try out a variety of part-time jobs or internships while in school. Get as much experience as you can.


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