How to Design Your Career Like an Entrepreneur

Join Penn Career Services and Penn Alumni Lifelong Learning for “Find Your Inner Founder” on April 24th, 2025, to learn more about how an entrepreneurial mindset can help you find or create meaningful work. Dr. Erica Machulak (C’09) will be presenting, and shared some of her thoughts on designing careers like an entrepreneur below:

I had heard so much about ImaginePhD while writing Hustles for Humanists that I decided to try it out for myself.[i] I was shocked and delighted by the results of my Skills Assessment. More than three years after launching my business, my lowest skill scores were in the job family “Entrepreneurship.” The results were determined by my own categorization of entrepreneurship-related skills as the ones where I “have more experience . . . but still need guidance.” For me, it was a welcome reminder that I, like so many humanists I know, love my job because it lets me learn and grow in the ways that I want to. The flexibility to chart my own path and build relationships through the process is what makes founder life so rewarding.

My encounter with ImaginePhD dovetails with the findings of my research partner, Andrea Webb, through qualitative interviews with students in Hikma’s Summer 2021 “Entrepreneurship for PhDs” course. Over the six weeks of this course, I brought together eleven PhD candidates and recent graduates to think through together how to leverage their experiences as emerging scholars for future career steps. Some participants were actively starting businesses or non-profit organizations. Others were seeking employment opportunities or simply looking for inspiration. Through interviews with participants after the course ended, Webb teased apart the intangible elements of the graduate student experience that are so critical to our professional development but often unacknowledged. As she writes, “While skills and competencies are part of doctoral training, the whole doctoral experience cannot be reduced to a list of competencies.”[ii] Webb’s research indicates that professional agency and participation in communities of practice are vital to the development of academic identities.

People who can write and teach and give thoughtful answers to difficult questions possess a rare skill set that is sought after across industry, government, and the social sector. Here are three entrepreneurial principles that can help you think more expansively about your value and your options.

Learning is a strength (not a deficit). 

I’ve always thought that the moment when one becomes a scholar is when they transition from the first-year-seminar bravado of “I know everything” to the more reflective “I now know enough to appreciate what I can contribute and just how much I will never know.” Great entrepreneurs follow a similar trajectory. Like great scholars, their sharpening awareness of their own specialization enables them to enrich entire fields and communities of practice. And yet, many graduate students believe that needing to learn things is an inherent deficit in our professional value. When that awareness leads you to focus on our limitations, you miss the point: your ability to understand what you need to learn and then fill those gaps is a huge value add for any employer or client. When reframed with self-awareness and intention, your curiosity can be the greatest strength that you offer to clients and employers.

Done is better than perfect.

How many of us have heard the mantra “done is better than perfect” in the final throes of our dissertations? It is easy to get lost in the weeds when you are writing a thesis on, say, postmodern architecture or the gender politics of early science fiction. In my case, I spent two weeks in a windowless room full of rare-book-library catalogs chasing down sources related to a fourteenth-century town/gown brawl at Oxford. For a hot minute, I was convinced that the St. Scholastica Day Riots were the key to connecting chapters that I was struggling to fit together. After months of writing in circles, however, I mostly relegated that content to footnotes and a blog post.[iii] By the final stage of writing, looming deadlines forced me to prioritize the ideas that would serve me best in my current moment.

While exploring new questions and directions is an essential part of creating something valuable, so is figuring out which rabbit holes are worth the chase. One of the great joys of entrepreneurship, for me, is being able to test big ideas in smaller bites and gather feedback quickly. For scholars used to polishing work to (near) perfection before putting it out into the world, this can be an uncomfortable process at first. It gets easier with practice and by learning to simplify your services. One critical tenet of early-stage start-ups is that testing the most basic version of your offer enables you to contain the delivery of the offer itself as you learn about your customer and refine your business model. Entrepreneurs have a name for this lowest common denominator: the “minimum viable product” (MVP). The MVP concept is often used in the context of early-stage development of technologies, such as the video game that can “only shoot zombies” or the early testing of Rent the Runway as an in-person dress-rental service.[iv] Whether or not you want to build something that you can automate and scale, developing your services incrementally will help you clarify your strategy as quickly and efficiently as possible.

Doing “the minimum” is a tall order for those of us who are used to overachieving and grappling with complex problems over long periods of time. If you can master this approach, however, you will be well positioned to learn faster, collect payments sooner, and design the next steps of your business more intentionally. In Testing Business Ideas, David J. Bland and Alex Osterwalder prompt readers to create and test a “Single Feature Minimum Viable Product,” which they describe as “a functioning minimum viable product with the single feature needed to test your assumption.”[v] They invite readers to share the MVP with customers, gather feedback, and then evaluate the total cost to create the product, customers’ satisfaction, and the number of customers who came on board.

Tailor your message for your audience.

One of the most valuable concepts for emerging entrepreneurs to master is the “value proposition,” a statement that one uses to convey to a customer how the entrepreneur’s product or service will benefit that customer. The value proposition is widely understood as a way of capturing why your business exists so that you can design an effective business model and marketing strategy. For example, a professional grants crafter might say to a client, “My grant-writing services will help you submit a compelling proposal on time and with less stress.” While the term “value proposition” and the constellation of jargon surrounding it can be intimidating to those who are unfamiliar with industry culture, the concept is intuitive for many humanists.

Let’s recontextualize the “value proposition” through humanistic principles of communication, reason, and audience, reframed through the lens of Aristotle’s three pillars of persuasion: ethos, pathos, and logos. These pillars simplify the value proposition into its basic rhetorical purpose: to persuade your target client that the thing you are offering will benefit them. These discrete components also enable more effective storytelling, as the reader can choose which components to highlight in a particular context and translate those elements into the most accessible language for a specific audience.

A value proposition is a form of communication that you can use to craft and share your story authentically to build professional relationships and surface opportunities. Tailoring your value proposition for your audience will serve you well in any career context, including articulating how your strengths align with the needs of a particular organization, finding professional contacts who share your interests, and helping colleagues and mentors understand what you want to do and how they can support you. The more you can clarify how your values and skills align with the priorities of diverse target audiences, the better positioned you will be to position yourself for known and unknown opportunities. 

Erica Machulak is a medievalist and the founder of the Hikma Collective. This post has been adapted from her new book, Hustles for Humanists: Build a Business with Purpose (Rutgers University Press, 2025). 


[i] ImaginePhD is a tool developed by the Graduate Career Consortium to help PhD students and graduates clarify their values and triangulate potential career pathways to which they are well suited—you should definitely try it for yourself. Imagine PhD, home page, accessed September 3, 2023, https://www.imaginephd.com/.

[ii] Webb, Andrea, Erica Machulak, Naomi Maldonado-Rodriguez and Asya Savelyeva. “Moving beyond the academy: Professional agency & communities of practice in navigating post PhD careers.” In Progress.

[iii] Erica Machulak, “The Role of Researchers in Public Protest,” Medieval Studies Research Blog: Meet Us at the Crossroads of Everything, September 8, 2017, https://sites.nd.edu/manuscript-studies/2017/09/08/the-role-of-researchers-in-public-protest/.

[iv] Arshpreet Kaur, “What Is a Minimum Viable Product (MVP)? Types, Examples, Benefits,” Insights—Web and Mobile Development Services and Solutions (blog), November 2, 2022, https://www.netsolutions.com/insights/what-is-a-minimum-viable-product-mvp/; N. Taylor Thompson, “Building a Minimum Viable Product? You’re Probably Doing It Wrong,” Harvard Business Review, September 11, 2013, https://hbr.org/2013/09/building-a-minimum-viable-prod.

[v] David J. Bland and Alexander Osterwalder, Testing Business Ideas: A Field Guide for Rapid Experimentation (Hoboken, NJ: Wiley, 2019), 240.

By Joseph Barber
Joseph Barber Director, Graduate Career Initiatives