On creativity, entrepreneurship & fulfillment with Working Self’s Rebecca Fraser-Thill

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There’s nothing like debt to light a fire under your ass.

At least, that’s what has me more motivated than ever to carve out a career that will hopefully sustain me (and then some). But whether it’s student loans or a desire to break free from our uninspired jobs or something else that drives us, we all chase that elusive “dream” job or career—sometimes we just don’t know what that’s supposed to look like and whether it can realistically be done.

Today, I’m talking with Rebecca Fraser-Thill of Working Self about these things and more in the first installment of a two-part career Q&A series. (I’ll have another guest next week!) Rebecca has spent the past several years crafting a life that’s equal parts fulfilling, attainable and sustainable—the trifecta for success, I’d say. And her blog is dedicated to making sure others can do the same. Today, Rebecca has some words of wisdom for those of you who are creatives types and somewhat new to the workforce.

Check out our Q&A below.

Working Self

Briefly tell us your story and how you came to become so laser-focused on what you wanted to pursue for a career.

I became laser-focused by meandering. That may sound paradoxical but it’s completely true. As I was graduating college, I was so afraid of not knowing what I was going to do with my life that I jumped into a PhD program right away. Wrong move. I had no idea why I was there or what I wanted to get out of the experience, so I high-tailed it out of there after receiving my master’s degree – even though the doctorate was Ivy League and fully funded. That’s when meandering took over: I moved to Maine, the state my creative soul had dreamed about since I was a preteen, and stumbled into a one-year gig teaching psychology at a selective liberal arts college there. That one-year position turned into an eleven year stint, to date, including some amazing opportunities related to my passions that are unfolding at this very moment.

I’ve also had the chance to be highly intentional about how much teaching I take on each year, leaving me room to build side hustles and try other avenues out, in addition to caring for my growing family on an “as needed” basis. Throughout my process of leaping in a panic, stepping back and walking away from something “great” that wasn’t great for me, I kept coming back to the same question: how does a person build a fulfilling life? I became so obsessed with that question that I created Working Self, my corner of the web reserved for considering various possible answers. The pursuit of meaningful work has been at the heart of everything I’ve done, and I love having a forum for exploring the “how” with others.

What myths do young people, particularly recent grads, buy into about jobs and careers? Can you dispel them?

While teaching college, I’ve found the most common myth to be the need to find THE career. You know, the one and only career that will provide lifelong fulfillment and joy. Fantasy alert! That simply doesn’t exist. That myth actually spins off a bunch of related myths: that we need to have a multi-year plan in order to succeed; that it’s better to wait for the “right” opportunity than dive into an opportunity you have at hand; that our major sets our path. These are all deterministic, A-causes-B-causes-C ways of thinking, which are not at all not realistic. Thank goodness! Life is so much more dynamic and exciting and keeping-us-on-our-toes than that!

The reality is that a combination of action, reflection, and serendipity carves most people’s career paths. We can’t see how our life is going to unfold as we’re starting out, but when we eventually look back on the years behind us, all the twists and turns make perfect sense. So after graduating you simply need to reflect on what you think you want at this moment based on your strengths and interests, take the leap and start DOING something, and then be alert to serendipity when it comes knocking. Then repeat the process over and over throughout your life. That’s how a career path actually unfolds – which I find to be a lot less daunting (and more thrilling) than the plot-and-plan approach most graduates think they need to take. My story is a case and point, and just one of many.

By the way, I enjoyed tackling this topic in more depth recently on Life After College – and, bonus, Jenny Blake and I offered a free webinar on the topic that is archived here.

Lots of people aspire to be entrepreneurs, but not everybody’s cut out for that kind of bootstrapping work. How can someone who’s uncertain tell if they’re meant to pursue a path of becoming his or her own boss?

I can certainly relate to this question: I’ve finally accepted that I’m not cut out for full-time entrepreneurship, even though I always thought that would be the right path for me. As far back as age 7, I began selling homemade greeting cards to relatives and neighbors! Entrepreneurship sounds great in theory: complete autonomy over scheduling and tasks; no boss to wrestle with; flexible work setting. In reality, though, you have to be someone who can withstand loneliness, work that grows to fill every single crevice of your life, and a lack of financial security.

I found out that full-time entrepreneurship is not right for me by building side hustles, which is the route I suggest everyone take. Side hustling not only allows you to test out your particular idea, develop a client base, and gain confidence about your potential income, it also lets you try out the less tangible aspects of entrepreneurship, like the hustling itself! While freelance writing and career coaching on the side, I discovered that I love to create but hate to sell, a combo that doesn’t have “full-time entrepreneur” written on it! Thankfully I have had the opportunity within my actual job to carve out entrepreneurial endeavors, which feed my creative needs while letting me off the hook on the sales front. It’s possible to think and act like an entrepreneur without actually being one full-time.

Having a fancy website design, sassy copy and professional photographs are all well and good (and important!) for anyone looking to catch potential employers’ and clients’ eyes, but what are the less sexy, more practical tools everyone should have in their belt?

I could use some of that “sassy copy” you mention! Seriously, at the basis of any job search or development of a client base lies the same thing: genuine relationships. You can have all the flash, but if there’s no substance beneath it, you simply aren’t going to get too far. I love the book Never Eat Alone by Keith Ferrazzi and Tahl Raz, which emphasizes the importance of building connections that have substance and are reciprocal. That’s the skill set everyone needs to get down pat to lead a life that’s meaningful and successful.

Networking isn’t about superficially seeking people out when you need something; networking should be done all the time, in every circumstance, with no ulterior motive at all. Those relationships are what yield the vast majority of job offers and client leads – either your own or another person’s. When networking is approached in this way, you become part of a giant web of helping and sharing, which is fulfilling in and of itself.

Are creative types doomed to constant debt and worry, or are there ways we can armor ourselves against falling victim to the unpredictable creative landscape?

I hope we’re not doomed! I actually think we overestimate how much security “regular workers” have. The reality is that we are ALL at the whim of the economy, as we saw during the last economic downturn that left thousands unemployed for long stretches of time (and many still are in that boat). If anything, I think creative types are better equipped to handle economic shifts than people who do not identify as “creative.” We creative types are used to taking an existing “problem” and coming up with a novel solution; that’s our bread and butter. So when the landscape changes, we’re ready to say, “huh, maybe I can make money doing X, Y or Z.” It’s all about staying mindful about the convergence of what the world needs and what we have to offer (and creatives have multiple offerings, by definition), then matching the two together as those needs shift.

Any final thoughts to add?

If you want to create a life you feel good about, you have to be prepared to have people scratch their heads about you. The vast majority of my big decisions have been incomprehensible to everyone but a handful of people who know me extremely well. I used to let that bother me, and sometimes would make the “understandable” decision because of the pressure. I see many of my former students take the easy route, too, and I feel badly for them because I know that while they’ll enjoy others’ acceptance, they’ll never enjoy their own acceptance. And the latter? That’s what really matters.


Thanks, Rebecca!

Enjoy what she had to say or have any thoughts of your own? Let us know in the comments. And make sure to come back next week for part two, featuring a Q&A with the founder of One Woman Shop.

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  1. I loved reading everything Rebecca had to say!! So much of this post rang true for me and it was great to hear it from someone else. I am a recent college graduate (hello May 2014) and I have been bouncing around not really “doing” anything because I thought I need to wait it out and see if the right thing comes to me. But you know, I really needed to hear some of these things and to get a fire started under my own butt to get me moving. So here’s to new opportunities and a clear mind (hopefully)!

    • Congratulations on graduating! Right things rarely just appear. Serendipity definitely DOES play a role in our path, but from all that I’ve observed and read, it happens when we’re being active agents in our life WHILE remaining open to possibilities and connections. At the times I manage to strike a balance between reflection and action, I find that life works best.

      • Cassie Paton says:

        So glad this struck a chord with you! I’ve had the tendency to wait it out in the past too, primarily because I’m so damn indecisive. But I’ve made improvements on that recently because I can’t afford to be indecisive anymore. So far, my instincts haven’t steered me wrong yet, and it’s nice to have a newfound confidence in my decision-making abilities.

  2. This is great advice, especially since I’m starting to worry that I’m not necessarily cut out to be a full-time entrepreneur…but I’m not quite ready to give up that dream just yet =]

    • You might never have to give it up totally! We can be entrepreneurs in so many forms in so many different settings. I am entrepreneurial, but not fully an entrepreneur. Best wishes on your journey!

      • Cassie Paton says:

        I have aspirations of self-employment, too, but I’m not sure I’m cut out for doing that full-time either. I’m definitely envisioning multiple jobs at a time in the future, which is fine with me—I just hope to find balance.

  3. Such a fantastic (and incredibly encouraging at this point in my life) piece, and one I am sure to continue to draw inspiration (and strength) from, as someone who always feels like searching for a ‘forever’ job and career is something I have to do; it’s great to read (and listen to) advice that dispels that myth.


  1. […] you would like a little something to read over, though, check out the terrific interview Cassie Paton at Witty Title Here recently conducted with me. We chat about all things creativity, entrepreneurship and – indeed – creating a […]

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