One of the pre-programme assignments given us, as fellows of the Asia Pacific Leadership Programme of East West Center, was to identify three individuals in Hawai’i whom we would like to meet and to subsequently carry out an informational interview during the programme. I decided that my informational interviews would be of social entrepreneurs as I had just started an enterprise at the beginning of 2012 and which I hoped to expand to a social enterprise. I came across a 2007 Hawaiian news article that mentioned the 25 Hawaiians to watch out for the next 25 years and I decided that I would reach out to three of the social entrepreneurs mentioned in that article. The following is a summary of my interview with Cheryl Ka’uhane Lupenui (Hawai’i, 27.08.2012)

Cheryl Lupenui is the founder of The Leadership project, a social enterprise based in Hawai’i and a board member of the Hawai’i State Department of Education. She was  the former chair of Young Women’s Christian Association (YWCA) and has  also served on the Resource Advisory Board for the Tourism  Authority in Hawai’i, Organization for Women Leaders (OWL), national board of the Center for Asian Pacific American Women and on the community-building committee for Aloha United Way.

Source: The Center for Asian Pacific American women

Working at YWCA

Cheryl Lupenui comes from a business background and was introduced to business with a philanthropic mission through her work at YWCA – an organization functioning over 100 years. YWCA has a business model tied to social enterprise. The primary revenue source for YWCA is mostly through fee-based services and a smaller percentage through philanthropic services. The YWCA mission is mainly focused on empowering women and eliminating racism within the national mandate of freedom and social justice for all people. The local state organization, focused on health and well-being, economic and leadership development, is part of the state-wide network, national network and international network.

Cheryl’s initial work at YWCA started with the restaurant and she created a venue for youth through culinary art. Her roles and responsibilities grew and eventually, she became the Chief Executive Officer of YWCA, where she worked for 10 years. A key challenge that YWCA has faced, according to Cheryl, is the struggle to continue to be a viable organization locally and across the country and internationally. One of the reasons is that women are really busy and YWCA counts on the presence of women. So, her primary challenge was to re-convene women with matters that are important to them, while overcoming the bigger challenge of their making the time to be part of a community.

With that objective in mind, Cheryl thought about what women shared in terms of a story, irrespective of how much money they made. Not poor vs. rich but what they commonly struggled – a work/life balance. First, she started with aligning a community on how we support each other and then as a community to champion for common causes, in terms of social justice. A lot of the new initiatives, setting the table for social change, dress for success, women leading change etc. were tied to that initiative.

Challenges and Lessons learnt

Cheryl considers that what she is doing now is based on lessons learnt and experiences from her work at YWCA. The biggest challenge, she faces in her work, is bringing a sense of community back.

One of the lessons that Cheryl learnt from her experience is when she raised the question about who else cares about women’s empowerment, she found that men surprisingly rose to the top. The initial assumption she had was that women should deal with their own empowerment but women tend to put themselves last. Whereas she found that men were clear about the reasons why women and men needed to invest in women and causes they believe in. It was interesting to come to that conclusion. So, she felt that it was good to have men at the discussion table, partaking in the conversation, and share in the leadership of the YWCA’s mission. The challenge was how to engage men and women as equal partners.

An example that strove to address this challenge was the LifeInc project – national school programme which was modified and brought to Hawai’i. The unique addition was that YWCA had approached businesses and asked for young adult volunteers, in their twenties, who would go into schools and volunteer as mentors. It was a team approach and there was a five member team so that at least one would show up for each class but usually all five turned up. Both male and female youth were included as volunteers – the volunteers practiced leadership skills and community service which was good for their businesses and the students learnt a lot from their mentors.

The Leader Project

Cheryl left YWCA around a year and a half ago and started her own company called The Leader Project. Cheryl had known what she had wanted to do but initially, she had wanted to work in an organization. However, she didn’t find anyone who was doing what she did and so she decided to start her own company. Her company focuses on leadership, from a Hawaiian worldview and a western worldview. Her leadership models are based from her experiences in studying leadership, leading at the YWCA and in community, and also providing leadership programmes for women in Hawai’i. She strongly felt that leadership models that we are familiar with are from a western perspective and that as a Hawai’ian woman and somebody who is here in Hawaii, Cheryl had felt that the leadership wisdom that the Hawaiian culture brought was being missed out. Particularly as she believed that we should honour what different cultural worldviews with respect to leadership means as there is no one way of leading.

Cheryl particularly wanted to blend her two worlds. Born and raised in a very western environment outside of Washington D.C. and ethnically, being a Hawaiian, Chinese, German, Italian, French and English, Cheryl has lived in Hawaii for longer than anywhere else and felt very rooted and at home in Hawaii. Her key question to herself had been “I am a businesswoman. How do I bring these different worlds together that of a Hawaiian businesswoman instead of being Hawaiian in one place and a businesswoman in another place?” She had felt that she was living dual lives for a while and felt the need to integrate both lives. Her company provided the space for her to bring her two worlds together and operate from that intersection and find others who would value this type of leadership development, not only value the perspective of the Hawaiian indigenous culture. Cheryl feels that she doesn’t train in the traditional sense. She named her company ‘The Leader Project’ because she likes doing projects and because she believes that “when we create projects as leaders and go through that together, we put into practice leading then that further develops us as leaders. That process is taking all that theoretical concepts and putting into practice and that is when it becomes really embedded – when you are actually doing it.” Cheryl particularly likes doing group process and projects where there is a start and an end and the outcome and results can also be quantified. She considers it a different way to enter the leadership conversation and that the journey so far has been good and that she has been able to make a business out of the idea as well as continue her volunteer work.

The Leader Project is a social enterprise. It was set up as a for-profit business and at its core, a social mission. Cheryl felt that she wanted to keep her enterprise simple and didn’t want a board of directors, staff and a lot of administrative work. She wanted to create a sustainable revenue source. She wanted the work to be valued by a western sense. She feels that a lot of the native programmes are funded through Government funding which can perpetuate a “poor and needy” conversation – “it is a story of a lower social income rung on the ladder, the statistics only look at economic measures of success – that is true, those are facts but I want to talk about strengths and other measures of success. Our people. Our place – Hawaii. About abundance and strength. For people to value it because it is really a gift. We pay a lot of money for western leadership, why wouldn’t we pay for other cultural leaderships? It is kind of a test to see whether it could stand as a business. To make it a profitable, a viable business that does social good work is a lot harder.”

Being a social entrepreneur

Some of the challenges Cheryl has faced while building her social enterprise is that she can only take on limited projects as she is the only one involved but at the same time, she has to build a pipeline so that there is income coming in. The challenge is particularly so if there is a very profitable project but the people or organization does not really value the Hawaiian culture. That is where Cheryl feels she has to be careful about – “even if it is profitable but if their actions do not value your core beliefs of valuing Hawaiian culture, then it is better to walk away. To believe that there are enough other people who walk the talk.” Another challenge that Cheryl faces is that she finds it hurts when people in Hawai’i do not really value Hawaiian culture. She sometimes feels that people outside of Hawai’i value Hawaiian culture more than some people here.  “This is the only Hawaii we have in the world. I do not care if they don’t hire me or value me but that is crazy if they do not have some value for the root culture.” It is in those moments that she sometimes feels she wants to give up and when she sometimes questions herself about the practicality of having a steady job and stable paycheck. She continues to face these moments but it’s been a year and a half since she set up her company and she feels she is now stronger and less tipped over or knocked off-center. Especially because she has seen the impact that her work does and she has decided to stick to it. Cheryl initially had decided that she would give it a year and see if it worked and has found that she enjoys her work a lot and has decided to continue. “Right now, I am in a good point and I would like to continue for some time to come.”

One of Cheryl’s key realizations is that she can contribute in a meaningful way, not because of her title or position, and not in isolation but with people. She feels that she gets to bring something unique to a larger   conversation and be part teacher/ part student and that she can really enjoy work everyday and the people she works with. The challenge she felt is getting used to not having a title and a reputation and being just herself. She suddenly felt that she was not anybody and she realized that much of her identity had been tied to a position. It was a vulnerable situation to be in as wherever she went, she went as herself. “It is not like here is my position, here is my other life. Everything is here – right on the table. It was difficult.”  Once she crossed the hurdle, for the most part, the joy/ great moments are just doing good work with people and having caring relationships in her work. The common goal that they are working together to make a meaningful difference whether it is in education, social services or youth, and particularly that she is just one piece.

Appreciating life’s blessings 

Growing up in the east coast, Cheryl felt that it was very much achievement oriented. It was always about getting an A in a paper, going to college, there were very much these benchmarks that she was taught that you do and you keep climbing up that ladder. It was great but she realized that she was missing a lot along the way.  She felt that the singular, individual mindset was kind of selfish and she credits her husband for being the first person to wake her up. She feels that he has been a gift – good at reminding her of what is important – “This is achieving a goal. This is living. It was a lifelong lesson to shift my mind to what really is important. Particularly in this results-oriented world. Nobody gives you a bonus for stopping and looking at a beautiful sunset. It is a priceless gift. It is nice to live that kind of life– that does not miss out. I feel I had missed out as I was so internal focused.”

She strongly feels that work is not separate than life. “You are who you are, wherever you show up. Compartmentalizing yourself is not fully living. It was not until I realized that this is everything. I bring all of this whether I show up at a board meeting, project meeting or my husband’s meeting or whatever it  is. I am fully all there. That was a hard lesson. It is part of every day. So, “being here is getting there” is just appreciating that this given moment, this time together, what it offers, beyond even just the beautiful sunset – the opportunities.”