An Open Letter to Restless Young Entrepreneurs Who Can’t Wait Any Longer

To all young, motivated, frustrated people fighting to do it their way:

It me leading a discussion group at the University of Nebraska-Omaha recently

One great thing about having a long online record of founding and failing businesses, taking risks, messing up, receiving wins, and sharing my thoughts throughout the course, is the conversations and relationships it initiates with readers. I often receive emails or otherwise communicate with people who are desperately longing for some creative or professional satisfaction that they are struggling to find. Sometimes it’s fed by frustration about feeling obligated to some false expectation of responsibility placed on you by others. Sometimes it’s that you did everything “right,” but that checking accomplishments off of life’s to-do list didn’t give you any fulfillment or gratification. Or maybe it’s just not knowing how to stop the hamster wheel without having everything else in your world spin out of control.

I want to extend this conversation here and share my feelings about what you can do if you are feeling this sense of exasperation, helplessness, panic, and chaos.

First, keep in mind that this is my opinion from my experience — the experience of a woman like me in a context like mine — and I can only generalize. However, maybe this will be a jump-off to realizing what is right for you.

If you are in college, finish your degree. Just getting accepted into a school and being enrolled in classes means you are already so close. Your degree will be an advantage that follows you everywhere in life, and even if you are struggling to find something to be passionate about in your studies, I believe you can reframe your perspective to make your educational experience mean something to you. There is immense value in the experience itself of receiving a university education. College is not really about the degree at all. When I see job applicants with four-year degrees, that tells me they are able to commit to a process of rigorous, structured work (one hopes). It sometimes shows me, when combined with a CV, some references, and a good interview, that they can work within a bureaucratic system to affect change, progress, and reach their personal goals (a.k.a. the real world). However, college degrees do NOT indicate intelligence, passion, discipline, emotional intelligence, or curiosity, which you know already. Which can be the frustrating part. It is never a bad idea to have a college degree, but getting a degree for a job is a bad bet. Getting a degree for the knowledge, skills, experience, and relationships you form while earning it is a good bet. Educating yourself is good, whether through traditional paths or unconventional ones. It’s my experience and opinion that college is a very good resource for people who are interested in educating themselves. If it is convenient and possible for you to attend college, or if you are already enrolled, I don’t think you will ever regret making the most of it.

As an important side note, you don’t need a degree to have most jobs. Even most good jobs. That is not a thing anymore. You can persist your way into so many things. I do not believe in deluding kids into thinking that their degrees either purchased by their parents or by saddling themselves with years of debilitating personal debt entitle them to an unpaid internship at a cubicle farm, let alone a full-time job. A degree is a privilege. It’s a way to hone a skill and earn knowledge that you are going to love and continue to develop. You get a degree because you want it, because you love what you study, not because you think it guarantees you a job. Odds are, a degree will help you get a job. But that’s because of a system that prioritizes a very privileged type of learning over another, and the exciting thing is that fewer and fewer innovative companies that are hiring have respect for that system. With that caveat, I only wanted to say something specifically to the restless, ambitious kind of young person who is lucky to be comfortably enrolled in school and is thinking about leaving. To them, I think you should take the educational opportunity as the gift it is, and make it work better for you.

Many entrepreneurial and creative people are uncomfortable with the idea of structure and conventional paths. For me, “normal” models of life’s script, the landscape of educational institutions, and the outside pressure to not fuck it all up were easy to question because I feel naturally opposed to traditional models of work/success/life. As a restless, ambitious person, you probably know what I mean. But it is possible to use systems and structure to enable your success, whatever that success looks like to you. And that structure can actually be on your terms. You can define the structure that facilitates your motivation and success, and frame your experiences within it. When I felt this way in college, I put my frustration and hunger into my studies and got really focused on being the best at one thing that I really loved. Propose an independent project. Lead something. Design the experience you’d rather have. Insist on taking value from this wonderful opportunity. I was studying subject matter that I did enjoy, but did not expect to pursue a career in — intercultural communication, German, and radio, which I admit caused some worry. I was eager to learn about these subjects, and my enthusiasm made it much easier to extract lessons and skills that I could apply to literally any other experience I wanted to pursue.

Travel. Do freelance work to build your name and field of experience. Be helpful. Do all of this as soon as you can. You can do freelance work while you are in school. You will have as much if not more time to travel as someone with a more conventional life experience, so find the pockets of time you can use. Find reasons to go, find work to do in other places, and develop relationships that nurture and support your tendency to seek.

I never resigned myself to a fate other than the one I wanted as an artist and entrepreneur. That, however romantic, is where the self-assuredness ends. I didn’t know what shape my career would take, I was just happy to be working jobs I enjoyed on my own terms, and that they always seemed to lead to something new. I started embroidering in my apartment and it led to a formidable stack of magazine and blog features, which led to working with 400+ brides/year, which led to opening Omaha’s first coworking space, which led to operating Princess Lasertron in a 2000 sq. ft. studio with four employees, which led to my dress line, which led to founding Hello Holiday and closing the old office and pushing the lease off on someone else, and focusing full-time on finding a way to make space in my life for everything that fascinates me. (That entire last sentence probably contained a handful of prescription medications, several serious phases of wanting to shut it all down, my first book, six years of counseling, 12 bottles of celebratory champagne, a divorce, a baby, one broken finger from punching a wall, and countless fist pumps and tears of happiness, by the way. The right choices haven’t usually been obvious.)

You have to find that confidence in yourself — not blind, unchecked self-assuredness, but maybe just the mere belief that you will do right by yourself.

Be aware of why you are doing things. Reasons can be very motivational, and the real ones may not be the first ones that come to mind. Once I know why I want things, once I have something to stick to the center of my dart board, the rails I gotta ride become a lot smoother. The hassle of the work it takes, the compromises, the getting along, the playing the game, everything I would normally be frustrated by, is less tragic. I even wonder if I wasn’t honestly being a little whiny. You aren’t entitled to an easy go of it, but finding creative ways to reach unconventional goals makes these challenging transitions more meaningful.

Working for others or having other jobs is not selling out. It doesn’t have to crush your soul. If you’re saving to start a new business, or if you’re paying for school or travel, you have to get money somehow, and it doesn’t mean you’re a “corporate slave” or some other messed-up rude term you heard from some rich white startup founder’s dumb keynote.

Even if you already run your own business, there’s absolutely no shame in getting some extra income on the side when you need it. Personally, I host on Airbnb, like, daily. I have done a significant amount of freelance copywriting this year. Anything anyone wants from me, I am pretty much willing to put a price on. In all of my side work, I don’t do it because it’s my “passion,” it’s because I need the damn money and I don’t dislike earning it that way. For me, “not disliking” is enough when I really know what I want and why and what I’m doing to get it.

I hope that you reach out in your community to meet with influencers, leaders, people who are doing what you want to do, people who might have ideas or suggestions, and people who are stuck too. Anyone. I’ve learned that helping others is the best way to help yourself–it sounds beyond corny, but I really mean it. If someone needs something and you can help, offer it. It’s the best way to challenge yourself, learn about what other people are working on and accomplishing, and honestly it’s a great way to get noticed which is invaluable when you’re in these places of transition. The thing that will bring order to the frustrating chaos is relationships. There is no way to find these opportunities without taking the risk to put yourself in situations with people who are new to you.

Finally, please, above all, care for yourself. Preserve your physical and emotional health. Be gentle with yourself and kind to yourself. Never sell yourself short–you are good enough. Show the world why you matter, don’t wait for it to ask you. Be very, very brave.


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