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The Rise of the 'Side Hustle'

in Student Affairs

How Entrepreneurship is Changing the Future of Higher Education

· Higher Education

Synopsis: Due to financial uncertainty, generational shifts, and conflicting personal and professional values, many student affairs professionals are beginning to share their talents with the world through entrepreneurship and 'side hustles'. Given their many transferrable skills and natural leadership abilities, student affairs professionals are well-positioned for entrepreneurship. With insights from Dr. Kathy Obear, Dar Mayweather, Kayley Robsham, and Michael Alexander Lemus, this essay explores the ways entrepreneurship might be an innovative solution to many of the problems facing higher education. (20 min read, 7 min skim)

Entrepreneurship is becoming more and more popular among student affairs professionals.

From consulting, coaching, and speaking to selling art or driving for Uber, many student affairs professionals are sharing their talents with the world through entrepreneurship and side hustles.

To learn more about the rise of entrepreneurship in student affairs and higher education, I interviewed Dr. Kathy Obear, who has been in business for herself for over 30 years providing organizations with training, speaking, and facilitating around issues of social justice and inclusion. “I’m excited to see lots of folks doing entrepreneurship from student affairs,” shared Dr. Obear. “When I’m at conferences, I see workshops on entrepreneurship that are filled with 100 plus people.”

“I’m excited to see lots of folks doing entrepreneurship from student affairs. When I’m at conferences, I see workshops on entrepreneurship that are filled with 100 plus people.”

- Dr. Kathy Obear

An Alternative Source of Income

The cost of living is going up in the United States, student loans are the second highest form of debt in the country, and there are less resources being dedicated to student affairs divisions within colleges and universities. This means that the salaries for many student affairs jobs are barely enough to cover the minimum living expenses in many locations around the United States. In places like San Francisco or New York City, the wages for a student affairs post are often not enough to cover basic needs like housing, transportation, groceries, and healthcare. As a result, many student affairs professionals are turning to entrepreneurship as an alternative income source.

I spoke with Kayley Robsham, spiritual business coach, founder and CEO of the Higher Ed Entrepreneur, moderator for the Student Affairs Entrepreneurs and Side Hustlers Facebook group, and creator of the SApro to CEO entrepreneurship training program. Robsham noted the the need for financial stability as a motivating factor for her to pursue entrepreneurship. “When I took the leap of faith, I actually didn’t have enough money to pay my bills. The work that I had to do was around money healing. Even now talking to student affairs professionals and higher ed professionals the salary is too low for so many people,” noted Robsham. “To be able to fill up your own cup in terms of money… people are looking for that right now.”

“To be able to fill up your own cup in terms of money… people are looking for that right now.”

- Kayley Robsham

Additionally, I spoke with Michael Alexander Lemus, founder of Reclaiming Your Happiness with Lemus, who recently left the field of student affairs to pursue entrepreneurship. “The pay was not enough for where I’m at in my life. I needed a side hustle or I would have to leave. Student affairs professionals like to say they don’t do it for the money, but we need money. A lot of people experience financial struggle and in many places salaries cannot support the cost of living,” noted Lemus. “Student affairs is going to lose people when they realize they can use those same skills elsewhere and get paid almost double sometimes.”

Generational Shifts

In addition to being motivated by financial need, the rise in student affairs entrepreneurship may also be a due to generational shift. A majority of the new professionals entering the field of student affairs are Millennials, and even some emerging from Gen Z. These young professionals are bringing a new perspectives and expectations about their careers, what is increasingly being referred to as “the Gig Economy”. According to the CEO of Intuit, Brad Smith: “The gig economy [in the U.S.]… is now estimated to be about 34% of the workforce and expected to be 43% by the year 2020.” Access to entrepreneurship has increased in recent years through the rise of the gig economy, including Uber and AirBnB, making it easier for everyone to be their own boss.

“The gig economy… is now estimated to be about 34% of the workforce and expected to be 43% by the year 2020.” 
- Brad Smith

Additionally, more and more aging Baby Boomers are in need of financial support from their family members – a phenomenon being called “The Silver Tsunami” – adding additional motivation for millennials and Gen Zer’s to earn more income through entrepreneurship. “There are so many millennials and Gen Zer’s in the field right now who are caring for their elderly. There is such a lack of support. And, that can be expensive,” noted Robsham. “So, millennials are draining their bank accounts in order to meet the needs of their grandparents or even their parents.”

Personal and Professional Values

I interviewed Dar Mayweather, diversity and inclusion speaker, trainer, and scholar, who began exploring entrepreneurship as a way to find more alignment and fulfillment in his career. “There’s not a lot of upward movement and mobility in student affairs and higher education. Where do you go when you feel stuck? That’s one of the things I felt,” shared Mayweather. “How many lateral moves do you have to make before I actually move up?”.

“There’s not a lot of upward movement and mobility in student affairs and higher education. Where do you go when you feel stuck?"

- Dar Mayweather

Moreover, declining budgets and calls for efficiency in higher education also contribute to low retention rates. The culture of neoliberalism in higher education tends to place extremely high expectations on Student Affairs professionals, which causes stress, anxiety, and for many, the desire to find professional fulfillment elsewhere. “Many higher education organizations are so toxic and dysfunctional, in my opinion. Entrepreneurship could be a way for folks to feed themselves emotionally and spiritually,” noted Dr. Obear. Adding to this sentiment, Robsham said, “Being in an environment that doesn’t align to who you are – your integrity and the responsibility you have – it can really weigh on you.”

For many, working for educational institutions, which are increasingly being influenced more and more by private corporations, with values that do not regard education as a public good. These corporate values include racism, sexism, consumerism, competitive individualism, surveillance, scarcity (Museus and LePeau, 2020). Entrepreneurship may be providing these college educators an opportunity to make a living by doing work that aligns with their personal and professional values while also promoting a healthier work-life balance.

"Many higher education organizations are so toxic and dysfunctional, in my opinion. Entrepreneurship could be a way for folks to feed themselves emotionally and spiritually."

- Dr. Kathy Obear

Mayweather highlighted this point by saying, “I think student affairs, in a lot of ways, mirrors society. So, society is all revved up about entrepreneurship and we have these students who are coming out of society – 18, 19, 20 years old – traditional aged students are coming onto campus and they’re saying they want to make money. You’ve got students graduating who are not necessarily interested in going to work for someone who is 40, 50, 60 years older than them and telling them what to do. They’re not necessarily interested in buying into these companies value systems that really aren’t there.”

Kayley Robsham’s journey into entrepreneurship was fueled by strong desire to align her career with her values. “After graduate school, I moved into a higher education technology startup company. I was the first queer White woman and the first woman. Working in a male-dominated space was eye-opening. I worked there for a few years doing marketing and realized a lot of the injustices for People of Color in mostly white workplaces. That lack of conversation and lack of support in the workplace actually made me realize that I can build my own business. I found out I was severely underpaid compared to some of my co-workers,” shared Robsham. “I really wanted to build a business that could be more inclusive.”

"I thought everyone would care about social justice, but I realized that not everyone was interested."

- Michael Alexander Lemus

Michael Alexander Lemus was also drawn to entrepreneurship as a way to live his values more authentically. “I can impact people in significant ways in and/or outside the field,” noted Lemus. “A lot of people graduate their master’s with rose colored sunglasses. We think we’re going to be able to change the world. I thought everyone would care about social justice, but I realized that not everyone was interested.”

Transferrable Skills

Perhaps another reason side hustles have become more popular among student affairs professionals is because these educators are particularly well situated to be successful entrepreneurs. Working in the field of student affairs typically develops an expansive set of skills and experiences that are particularly helpful in entrepreneurship. “I think there are a lot of transferrable skills that student affairs professionals have. Event organizing, social media, working with diverse groups of people… And, there are so many people in the community wherever you are that need help and they’re willing to pay people to do it,” noted Robsham. From accounting and budgeting to event planning and social media marketing, most student affairs professionals have already done many of the things that are necessary to be successful in entrepreneurship.

From accounting and budgeting to event planning and social media marketing, most student affairs professionals have already done many of the things that are necessary to be successful in entrepreneurship.

In addition to these tangible skillsets, student affairs professionals also have lots of experience working with people, which is essential for anyone exploring entrepreneurship. Moreover, the values of diversity and social justice are prominent for many student affairs professionals, which are also vital perspectives for anyone looking do business in today’s world.

Dr. Obear has observed that, “[w]hen new higher education leaders come in, Presidents or VPs, on average turnover 75% of their cabinet. There tend to be a lot of White women across sexuality and other identities that are being moved out, perhaps because of their identities and also maybe because they are speaking up to power more. I know this is also happening to a lot of folks of Color. When you speak truth to power and don’t stay in your place that’s defined by marginalized identities, people find ways to move you out. Folks with that level of leadership and experience with management and organizational change, those kinds of skills are so needed in executive coaching and team development within an equity and social justice lens.”

In the era of the cash-strapped university, student affairs professionals are well-acquainted with having to hustle in order to secure the resources necessary to help their office or department stay afloat. Robsham noted, “Another piece is that a lot of universities and colleges are closing. You need to have your own backup plan. Start making plans now, even if you do feel like you have a safe job. I believe the safety of a 9-5 job is an illusion because things can happen at any time. What is the future of higher education and how is it going to transform?”

“Another piece is that a lot of universities and colleges are closing. You need to have your own backup plan."

- Kayley Robsham

Whether acquired through graduate school training or on the job experience, student affairs professionals have a box full of tools to help build and sustain successful businesses. “We have some really talented folks out there who really want to meet people’s needs,” noted Dar Mayweather. “I think that’s what entrepreneurship is, at the heart of it. Someone has a need and someone believes that you as an individual can meet that need with overwhelming confidence.”

Naturally Entrepreneurial

In addition to having many transferrable professional skills, student affairs educators may be naturally inclined with talents that lend themselves to entrepreneurship. “The universe has been trying to tell me for many years to go be an entrepreneur,” shared Dr. Obear. “I’m not an inside person.”

Student affairs professionals are decision-makers, problem solvers, and first responders. They are innovators and achievers. Student affairs educators are, and always have been, leaders. What better people to step outside of higher education and share their skills and talents with the rest of the world through entrepreneurship?

Student affairs educators are, and always have been, leaders. What better people to step outside of higher education and share their skills and talents with the rest of the world through entrepreneurship?

For Mayweather, entrepreneurship has always been something that has come naturally. “I started my first business when I was like seven, doing a lemonade stand. I saved enough money for me and my cousins to go swimming every day for the summer,” shared Mayweather. As he got older and progressed in his student affairs career, Mayweather began to see opportunities for entrepreneurship sprouting from his work as a campus administrator. “I was asked to speak a lot on my campus before I became an entrepreneur. Only 10% of my time in my role in multicultural affairs was supposed to be spent outside of the office working with other departments, but it was working out to be more like 50%. I started thinking that maybe I could do this on my own.”

Complexities of Entrepreneurship

The rise of the side hustle in student affairs doesn’t come without complexity. I, myself, have been quick to point out the dreadful impacts of capitalism on higher education. Neoliberalism has turned higher education into a commodity that is bought, sold, and controlled in order to provide corporations with a labor force that is more interested in maintaining the status quo of passive consumerism and systemic oppression, than they are in active citizenship or building inclusive and equitable communities (Slaughter & Rhoades, 2004; Berg & Seeber, 2016).

Michael Alexander Lemus noted the dehumanizing effect of neoliberalism on his wellness when working in higher education. “When I was in student affairs, I felt like I was always trying to prove my worth,” noted Lemus. “Who are we trying to prove this to? It’s this invisible force. I worked 60 hours a week and weekends. I was always checking my emails. I was anxious about checking my emails. As I talked to more and more people, I realized that this is very common. People are looking for healing and for me, I never thought it would happen through starting a business, but it did.”

When I was in student affairs, I felt like I was always trying to prove my worth... I worked 60 hours a week and weekends. I was always checking my emails... As I talked to more and more people, I realized that this is very common. People are looking for healing and for me, I never thought it would happen through starting a business, but it did.

- Michael Alexander Lemus

Many have used capitalism to maximize personal profit at the expense of marginalized populations, like People of Color Women, and the Working Class. The economic system that has been used to oppress seems to be here to stay. But, if we are to resist the dehumanizing effects of neoliberalism in higher education, we must have individuals in every sector who value inclusion, equity, and the power of education to positively transform lives and communities. We must have visionary leaders, like those who work in student affairs, learning how to engage with capitalism in a way that promotes social justice, rather than contributing to the world’s suffering.

We must have visionary leaders, like those who work in student affairs, learning how to engage with capitalism in a way that promotes social justice, rather than contributing to the world’s suffering.

Enrich and Expand Higher Education

Though complex, entrepreneurship has the potential to enrich the field of student affairs and higher education. Robsham noted the ways that entrepreneurship can be a vehicle for student affairs professionals to promote the values of education in the world. She noted that many student affairs educators explore entrepreneurship “[b]ecause they see the impact they want to make and they don’t want to settle. I think entrepreneurship is that portal and it provides people who feel the need to want more and desire more. It’s there for them whether they want to stay in their student affairs job or not.”

While capitalism has been used to erode the values and practices of student affairs professionals, as we have seen with the escalation of neoliberalism over the past three decades, capitalism can also be used to expand higher education. Entrepreneurship is a tool, and like any tool, it can be used for many purposes. “Entrepreneurship allows you to go out, learn new things, realize how brilliant you are,” said Dr. Kathy Obear. “In some ways, folks – especially those with marginalized identities – might get seen and valued more if they are regionally or nationally doing work as a paid consultant.”

Some may be skeptical of student affairs professionals pursuing entrepreneurship. Understandably, many who oppose entrepreneurship argue that student affairs side hustles have the potential to distract and drain the profession of talented educators who would otherwise add value to their students and their institutions. The assumption here is that entrepreneurship takes away from a limited supply of resources that must be maintained. But in reality, entrepreneurship might actually result in more possibilities for the field of student affairs as well as innovative strategies to reimagine higher education. “Maybe talent isn’t being drained from higher ed, but we’re supposed to be somewhere else,” noted Obear.

Entrepreneurship might actually result in more possibilities for the field of student affairs as well as innovative strategies to reimagine higher education.

Currently, many institutions of higher education do not encourage employees to explore entrepreneurship. Whether discouraged through formal policies or unspoken expectations, many student affairs professionals would be at risk of losing their job if they publicly disclosed their pursuit of entrepreneurship. “I was really afraid of telling my co-workers that I was building my own business because I was afraid of getting fired. People who are at-will employees run that risk,” shared Robsham. Similarly, Lemus noted, “I was worried about leaving and telling people. But, it’s important to share because there are a lot of people who are going through similar things.”

Imagining New Possibilities

But, imagine if this wasn’t the case. Instead, what if these educators were encouraged to pursue side hustles? Rather than the current circumstances, which require student affairs entrepreneurs to either leave their jobs or hide their entrepreneurship, colleges and universities could develop policies that promote entrepreneurship as an asset to the institution. For example, student affairs professionals who are interested in offering their transferrable skills and talents to organizations outside of higher education, could be seen as advancing the work of the institution, rather than taking away.

Dr. Kathy Obear pondered on this possibility by asking, “Could you imagine if senior leaders, once a semester asked anyone who is doing consulting, coaching, or training on the side, or doing it intrapreneurially with other departments, to share what they’re learning? As you were out in the community doing work with non-profits, in the K12 system, or with community colleges, what are you learning?”

“Could you imagine if senior leaders, once a semester asked anyone who is doing consulting, coaching, or training on the side, or doing it intrapreneurially with other departments, to share what they’re learning?"

- Dr. Kathy Obear

Gaining additional professional experience with diverse populations, beyond the walls of academia, could be seen as a form of professional development. If student affairs entrepreneurs were supported by institutions of higher education in this way, college and universities might benefit by having a cadre of employees who are growing and developing their professional skills in ways that are mutually helpful for student affairs educators and those they work with through the side hustle.

Mayweather shared how entrepreneurship has allowed him to delve deeper into his passion for being an educator. “There are the people who advocate for others to get out of the field. Get out of students affairs. There’s no money. You’re not going to be happy. Get out of it. Then, there are people like me, who do entrepreneurship so that I can start doing the thing that I love in higher education. I used it as a conduit.”

“There are the people who advocate for others to get out of the field. Get out of students affairs. There’s no money. You’re not going to be happy. Get out of it. Then, there are people like me, who do entrepreneurship so that I can start doing the thing that I love in higher education.”

- Dar Mayweather

Mayweather also noted how for some, spending time as an entrepreneur can be a helpful exercise in realizing their true passion for education. “I’ve always been the person who said, ‘I’m going to be an entrepreneur but I’m also going to be an educator in higher education’. I’ve never felt like going on this journey has taken away from that,” noted Mayweather. “Sometimes it’s an opportunity for you to reset, get that focus, get back the steam and passion for whatever you had that you were doing and pursue it in a different way that you feel that you can be a lot more effective.”

Instead of being at odds with higher education, entrepreneurship could be valued as a way to promote the institution. Due to shrinking budgets and decreasing student enrollment across the country, universities are being forced to advertise themselves in new ways in order to attract students and their tuition dollars. Allowing student affairs professionals to venture out into the world through entrepreneurship could be a creative and innovative way for colleges and universities to promote themselves, and the excellent educators they employ.

Allowing student affairs professionals to venture out into the world through entrepreneurship could be a creative and innovative way for colleges and universities to promote themselves, and the excellent educators they employ.

Dr. Kathy Obear noted the benefits of entrepreneurship for the field by asking, “How can student affairs learn from this? What if the expectation is that it’s okay for you to be out consulting, but you bring along some of the literature to promote the brand of our organization? And, you’re spending some time doing one-on-ones or your taking names of diverse folks, who might be able to add value back to the institution. If it was an expectation that senior leaders supported and negotiated how much time people can be away and when, understanding that the value back to the organization is branding, marketing, and finding the next layer of folks that can come to the organization.”

Obear continued by saying, “None of us, in my opinion, have all of the talent and skills to do everything a department or an organization needs. Overutilizing internal talent – going back to the same director of LGBTQ Services, the same director of the Multicultural Center, the only Trans person in the organization, the only person who speaks Spanish to come and talk about all of Latinx students – the misuse and abuse of internal resources happens a lot. If there is a way there can be more resources within the region to share, everyone wins.” Indeed, some academic departments have policies which allow faculty to consult and share their research with others in order to promote the good work happening at the institution. Certainly, these kinds of policies may present complexities, but given the current challenges facing higher education, they might be a creative option worth exploring.

Embracing Entrepreneurship

Entrepreneurship has the potential to improve the field of student affairs and higher education. Student affairs professionals who are interested in developing a side hustle, or becoming their own boss, should think seriously about how they can leverage entrepreneurship to promote the principles that led them to higher education in the first place. Whether this means bringing the skills and experiences gained from entrepreneurship back to their work as college educators or advancing educational values in other industries, student affairs entrepreneurs should always strive to improve higher education and foster social justice in the world.

Student affairs professionals who are interested in developing a side hustle, or becoming their own boss, should think seriously about how they can leverage entrepreneurship to promote the principles that led them to higher education in the first place.

Several of the entrepreneurs I spoke with shared the importance of purpose and passion in entrepreneurship, as opposed to being motivated exclusively by money. Mayweather noted, “When I coach people on starting a business, that’s where we start… purpose. It’s not about how much money you want to make. It’s about who do you want to impact? It’s not about making more money. It’s not about getting more power and authority. It’s about what village are you creating and what kind of legacy are you leaving for the village?”

Dr. Obear shared a similar sentiment by saying, “If the motivation is to earn money, I believe most likely the universe will block you. For me, I need to get out of my own way. If I am in any of those really unproductive human ego-based ways, like self-centeredness or self-promotion, I probably won’t be useful because I’m not coming out of a full place of love. But, if it’s to be of service and you’re inviting abundance into your life… it might not sound different to people listening, but I do believe that is the spiritual balancing of both.”

With this bigger picture in mind, entrepreneurship is no longer simply a way to make more money for individual entrepreneurs. Rather, going into business can be an innovative and mutually beneficial way to support student affairs professionals and institutions of higher education into the future. Robsham highlighted one assets-based perspective of entrepreneurship for the field of student affairs by observing, “I think some people are being inspired by entrepreneurship. It’s actually helping their mental health while they’re in their jobs.”

“I think that employers should be talking about it because I have the theory that if you are happy in and outside of the workplace, there will be an increased retention of employees,”

- Kayley Robsham

College administrators who are working to find answers to the many challenges facing higher education might consider supporting entrepreneurship among employees as a strategic and creative solution. “I think that employers should be talking about it because I have the theory that if you are happy in and outside of the workplace, there will be an increased retention of employees,” shared Robsham. Instead of restricting the entrepreneurial spirit for fear that it might be a conflict of interest, administrators can develop policies that allow entrepreneurship in ways that benefit the institution and the employee. More than merely allowing side hustles, administrators may discover that encouraging entrepreneurship among student affairs professionals actually results in unforeseen benefits to the institution as well as the individual.

The future of higher education is more uncertain than ever. Due to economic and financial uncertainty, generational and technological shifts, as well as conflicting personal and professional values, entrepreneurship is growing in popularity among student affairs professionals. “More people are doing this,” added Lemus. “I hope that it gets more normalized.”

Given their many transferrable skills and natural leadership capacity, student affairs professionals are particularly well-positioned for entrepreneurship. While some believe that the rise of the side hustle in student affairs is problematic, there may be reason to embrace entrepreneurship as an innovative solution to many of the problems facing higher education.

But in order for entrepreneurship to positively impact higher education, student affairs professionals and administrators alike must begin to see the potential benefits of entrepreneurship. When we begin to think more expansively in this way, we can see more possibilities. And right now, more possibilities are exactly what is needed in order to reimagine higher education.

References

Berg, M., & Seeber, B. K. (2016). The slow professor: Challenging the culture of speed in the academy. Toronto: University of Toronto Press.

Slaughter, S. and Rhoads, G. (2004) Academic capitalism and the new economy. Baltimore: Johns Hopkins Press.

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