On isolation, authenticity & failure with One Woman Shop’s Cristina Roman

We hear a lot of words like “authenticity” and “failure” thrown around when talking about careers and businesses.

But these words are often used in big-picture terms, as though someone just starting out in her career should know what we mean when we use them. Today’s Q&A is part two of a career mini-series (see part one from last week here) that focuses on words in the context of careers and really getting specific about them.

I’m chatting with One Woman Shop founder Cristina Roman, whose community for creative solopreneurs addresses one word in particular: isolation. See what Cristina has to say below.


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

I think my friends and family would crack up if they heard someone call me “laser-focused”! I’ve always struggled with being pulled in a ton of different directions. Luckily, there’s a name for this kind of person, which I really identify with: multipassionate. It’s for those of us who love to dabble in various projects, always have our fingers in many pies, and love to learn just about everything.

That being said, I have found the common thread in my various projects and interests relatively recently: working with young women to find and thrive in careers and businesses that they love. Even more specifically, I now work almost exclusively with women who are starting or running their own solo businesses.

I do this through running One Woman Shop, a resource hub and community for female solopreneurs and freelancers, and offering business and career coaching and consulting, e-courses, and seminars through CMR Strategies in the areas of digital marketing, productivity, and personal branding.

And of the best parts of running my own business is that I can incorporate in any new interests I have willy nilly. That’s how my Unique Hobbies blog series and my Cultivating Happiness email series both came about, for example.

One thing your business touches on is something many people don’t talk about in entrepreneurship—loneliness and isolation. How does self-employment lend itself to those things and how can entrepreneurs combat them?

I would say that’s the number-one complaint of solo business owners and is how our tagline “going it alone doesn’t have to be lonely” came about. Entrepreneurs often start out working alone, either by choice or by necessity, and this can lead to a feeling of isolation, especially if friends and family don’t share the same passion for discussing the ins and outs of email marketing, the pros and cons of different legal designations, and the best strategies for finding a virtual assistant!

It can be tough working from home alone day in and day out, often going to a coffee shop doesn’t have quite the same feel as being in an office, and coworking spaces (shared office spaces for freelancers and entrepreneurs) can be expensive.

My advice for combatting this feeling of isolation: Meet other solo business owners in your area through Meetup, Twitter (try using FollowerWonk to search by area), and other local events; plan work dates and coffee dates to get out of the house; collaborate with other solopreneurs on projects and events, and set up periodic phone calls with people who motivate and inspire you (some of my most productive days have come after early morning phone calls that lit me up!).

We place a high value on authenticity in business these days, but that can seem like a double-edged sword for anyone just starting out who doesn’t want to offend potential clients or employers. How can any entrepreneur or corporate ladder climber walk that fine line while keeping her personality intact?

I think it comes down to making a decision: if there is a part of you that has the potential to offend or alienate someone – like your dirty jokes, your strong religious beliefs, or your political affiliation – and you choose to bring that into your business or the workplace, you need to own all of the possible repercussions. That could include not getting hired by a certain client or a company you want to work for.

Some people have made very successful careers for themselves by being 100% their “not suitable for work” selves – like Ash of the Middle Finger Project. This works for them, but it doesn’t mean you need to be the same way. It’s not inauthentic to have slightly different versions of yourself in your everyday life and your work life, as long as you don’t feel weird about it.

One Woman Shop

People talk a lot about failure as a positive thing. But what do you think they mean by that? Is there good failure and bad failure, and how can we use both to our advantage?

Failure sure is having its heyday, huh? It’s a complicated discussion because failure is all about perspective. For example, a $10,000 product launch could be an utter flop for one business owner, while it’s a gold mine for another. It’s also a matter of attitude – what one person considers failure, another may consider a learning experience. Basically, I think it’s all subjective!

The idea behind thinking of failure as a positive thing is that if you are putting out there over and over, you’re bound to fail sometimes. If you’re not failing occasionally, it probably means you didn’t really put yourself out there. In my opinion, it’s not absolutely necessary to fail, but it’s important to not be afraid to fail. And when you do fail, it’s crucial to learn from your mistakes.

At the risk of sounding too cheesy, we can use every failure to our advantage by learning from it. For example, I offered paid membership on One Woman Shop from the very beginning and exactly one person became a member in the first six months – pretty big failure, right? I learned that I needed to have a solid base of active individuals, prove that I provide valuable content, and poll my audience about what they were looking for in a paid membership site. Now that we’ve done those things, we’re relaunching our paid membership component!

How can someone just starting out build a community (online and in the real world) that will give her not only the audience, but the relationships necessary for upward growth?

Great question – we’re actually launching a coaching program around this idea! I think the first step is to cultivate resourcefulness and the ability to see the opportunities around you. Once you realize that opportunities to connect are everywhere, things get rolling pretty quickly. Another important piece is to make building a strong community around you a priority, not just something that falls to the wayside.

I firmly believe that community building is not a one-size-fits-all thing; for example, some people love online networking, while others thrive on making in-person connections. Some people build community through blogging, while others have find Instagram to be more suited to them. It’s all about finding your fit while still being willing to experiment.

Hands-down, my #1 recommendation is to get incredibly comfortable with direct outreach, whether it’s to ask people to join your email list, be a guest on your podcast, let you speak to their organization, or partner with you on a collaboration.

At One Woman Shop, we’ve been putting a lot of effort into high-impact activities, such as guest posting on sites like Design*Sponge, setting up a pop-up on the site, doing direct outreach to women we think would be a good fit for the community, and partnering with solo business owners on things like our 28 Tips for Growing Your Community freebie.


Thanks, Cristina!

Enjoy what she had to say or have any thoughts of your own? Let us know in the comments. And if this series hasn’t touched on something you’d like to see covered, let me know that, too!

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

get to work

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.

Why you need to set boundaries before you can do the work

Continuing with my guest post series, meet Lauren Caselli, the freelance writer and blogger behind Living Life Barefoot. Lauren gives some insightful advice about what it really takes to get your career moving forward.

guest post series

So you’re a college student. Or a writer. Or a designer. Or a stand-up comedian. Or someone who is an independent thinker that wants to make a big change in your career. You want to work for yourself. Or someone else. But not the someone else that you’re currently working for.

When I began entertaining the idea of making a big change (working for myself as a writer), I already had a full-time job. Like so many of you who also have dreamt of middle-finger-ing the Man (that sounds weird, but I’m going with it), I was stifled creatively at my day job and I thought I had the writing skills, dedication, and savvy to make an online business happen.

I scoured the internet, followed heaps of successfully professional bloggers, and read more “How To Work For Yourself” posts than are good for any one person to read. This research led me to believe that my startup life would be this seamlessly flowing current, 40-hour-a-week corporate job melding effortlessly into 40-hour-a-week freelance writing job. I’d switch from pantsuits to leggings, French braid to messy side ponytail, coffee to herbal tea.

But you know what no one tells you? That it can be really, really hard to get started. And no matter how many “10 Steps to Your Dream Life” posts your read? You still have a responsibility to yourself to set yourself up for success so that you can do. the. damn. work.

Freelance Reality
I think one of the harshest realities that I realized when I decided to work for myself was that my social life was going to have to suffer.

When I moved to Manhattan after college at 22, my life went something like this:

• Wake up. Make breakfast. Shower. Read the internet.
• Commute 30-45 minutes to work carrying gym clothes, change of shoes, rain gear.
• Work somewhere in the neighborhood of 8-12 hours.
• Leave work. Commute 20 minutes to the gym.
• Workout for 60 – 90 minutes.
• Shower (#2 of the day).
• Go to a lecture/meet a friend for dinner/get drinks at the bar/go see a show/attend a charity event/run a volunteer meeting.
• Go home.
• Eat something/pass out in bed. Maybe blog, but more often, not.

My weekends were filled with running clubs, brunch dates, outdoor adventures or weekend getaways. Sometimes, I’d fly to San Francisco for the weekend. I traveled to Aruba 4 times in 2009. I added 8 new stamps to my passport in 2010.

And this is how my life was, consistently, for five. solid. years.

Why am I telling you this? Certainly not to make you jealous, or to say “Look at all the things I’ve done! Look how great my life was with a corporate job and lots of free time and so much money!”

The point is, instead of finding a way out of the “meh” job that I held, I filled my life with other things that made me happier. It probably wouldn’t have been a bad way to continue except I was still feeling stifled and creatively shackled. So I made the decision to leave for good, to travel for a bit, to explore a new career path, and finally, to settle in Montana, a place free of distraction (save the occasional ski day) where I felt like I could focus. It was my very own Walden Pond. And it was the first step in setting myself up.

Except after five years of building a social life so full and vibrant, I didn’t know how to…well, not have that. I moved to Montana and went back to my old social habits. I went out with friends four nights a week, I attended potlucks and free cultural events. I went to yoga a few times a day so that I could simply be around people instead of alone in my house, facing a mountain of networking challenges and business building hurdles. In fairness, I was likely subconsciously clinging to something that felt safe in a new place where very little was familiar.

Boundary Setting
The truth was, I didn’t actually know how to work hard anymore. From my corporate job, I knew how to work until my job was done, and then I could turn my brain off and enjoy my life again.

But that’s not really how it is when you work for yourself or if you’re trying to find a new job. Your brain is always on, scrolling your To Do list, reminding you what still has to get done before bedtime. And more often than not, at least in the beginning, your brain isn’t reminding you to go to trivia on a Wednesday. It is reminding you to blog, pitch, rewrite your resume, create, design, brainstorm, email, follow up. It’s reminding you that you are the only one that’s going to get any of this done. It’s reminding you that you really need to try.

I needed to set myself up with boundaries and guidelines and sacrifices I was okay with so that I could get my work done. I had to quit the social scene. Not forever, but for a little while. Sometimes, just setting those boundaries is half the battle.

If you’re struggling to get started, or to find a job that you love, or make some real-deal progress in your career, here are some situations you may need to identify and work on eliminating:

• A negative relationship, whether with a significant other, or a parent or someone else who’s holding you back
• A negative job in favor of another (maybe not perfect but less emotionally draining) one
• Trolling the internet for validation, a “quick and easy way,” or “10 Ways to…”
• Making another huge life change because it seems “safer” (getting married, moving, finding a boyfriend/girlfriend)
• Feeling like you really want something else (like a relationship or living closer to your family)
• Feeling like you need to cultivate your town’s social scene every night or else you will devolve into a pit of anonymity and despair

You want to work for yourself, or actually find work that you love? Set yourself up so that you can. Eliminate (or at least minimize) whatever is distracting you so that you can single-task. So that you can organize and get some shit done. I’m not going to sit here and tell you to take a break for your sanity because, well, sometimes you need to be a little insane to do this self-employment thing, to live a life of which you are truly proud. And besides, you know when you need to take a break. You don’t need me to tell you.

What distractions do you find yourself keep you from doing your work? Have any of you imposed boundaries so that you can get your work done? If so, what are they?

Lauren CaselliLauren Caselli is a copywriter + content marketer. A Manhattan desk-jockey-turned-outdoor-junkie, she left her NYC apartment for the wide open valleys of Montana. A former fancy-pants party planner, she now works with small businesses to create sexy web copy, teaches yoga to + spends entirely too much time reading the internet. You can find her at her blog, Living Life Barefoot, or her website.