5 Things You Should Understand About Self-Employment

I debated about whether or not I should write this post. The title and content inherently scream 'rant,' and that's truly not my jam. I don't want to eat up blog space with that sort of negative content, whining about whatever is bugging me the most in any given moment. There's plenty of that to go around already. 

But feelings aside, it is objectively true that I run into a lot of professional obstacles because people simply don't understand what it's like to be self-employed, especially as a creative. In an effort to educate, be vulnerable, and explain some of my most frequent professional and personal decisions, I created the list that follows.

From my experience as a self-employed writer and career communication coach, these are the 5 most important and misunderstood realities of self-employment. These are the the most abused characteristics of my professional life, the things I so wish I could get you to grasp in our daily interactions as friends, family members, acquaintances, or strangers. I hope that the items listed will challenge your existing perspective on self-employed professionals, and help to improve your relationships with others who share my professional status.  

5 Things You Should Understand About Self-Employment

Photo by  Laura Ockel  on  Unsplash

Photo by Laura Ockel on Unsplash


1. Routine is vital, especially for creative work. 

Being self-employed requires a great deal of self-discipline. I am CEO and worker bee, Marketing Director and Writer, HR Director and Finance Director. I am personally responsible for balancing every single aspect of my work, and as a result, I wear a bunch of different--and competing--hats on a daily basis.

On top of that, creative work has its own set of rules, and there are unique challenges that come along with it. The capacity for creative work comes from a different internal space than more straightforward tasks like running data in a spreadsheet, or drafting emails. The effort to produce creative work requires a crap-ton of intellectual and emotional fuel, especially at the beginning of a writing session. This was earth-shattering for me at the beginning of my writing journey. I was totally caught off-guard by the fact that creative work takes so much fuel. 

Both of these issues--multiple hats and the nature of creative energy--are most easily managed by a consistent daily routine. I work from home, and am surrounded by my personal to-do list every time I get up to use the restroom or get a snack from the kitchen. I see errands that need to be run, and laundry that needs to be washed. Routine keeps me focused, productive, and more empowered to separate my professional and personal responsibilities. 

When I wake up, I put on my CEO hat and tackle strategy for big-bucket priorities. For the next couple of hours, I put on my Consultant hat, making sure my clients' needs are met with excellence. If client work is slow, I put on my Marketing Director hat to develop communication plans, blog about my services, and share success stories. I do what I can to identify new clients, and reach out to new people whom I believe I can provide a meaningful service for.

After lunch, every single day, I put on my Writer hat. As much as I want to fight it because the work is challenging and vulnerable, I sit my butt in my office chair and make myself write. And at that time, every day, by body recognizes that it's time to write. The creative mind 'wakes up' and responds naturally. When I start writing at the same time every day, the hardest part is over, and the words flow freely. Some days are better than others, but the consistency of sitting down to write at the same time every day is huge. 

Disruptions that seem minor--like a doctor's appointment at 1:30 PM--are anything but minor. Trying to write at a different time of day is like trying to push a semi truck uphill, by myself. The next day, when I have no disruptions, my body is not in its usual rhythm. It requires a great deal more effort to get the creative wheels turning, to 'reset the machine,' so to speak. 

That effect is multiplied for larger routine disruptions like vacations. Being away for several days creates an avalanche of mental clutter that I have to clear out upon my return. On top of the time spent away from my desk, I lose a significant percentage of my returning productive time because it takes so much effort to reset the clock. It's true that commitments like doctor's appointments and vacations are inherently good things--of course they are! But that doesn't change the impact that these appointments have, so it is absolutely fair to name them as disruptions for my professional routine. 

2. Professional self-worth is a constant challenge.

The world sends me constant messages that my work is invalid because I haven't sold a book yet, or don't make a certain amount of money each year. We'll explore that more in Item #4. But on top of that, there are little voices in my head while I serve my clients or work on my novel, whispering lies about my professional identity:

You have nothing important to say.
You aren't really helping anyone.

You will never finish this book.
You have no idea what you're doing.
Nobody will ever buy this.
You are a terrible writer.
You are wasting your time. 

This is daily, people. Independent of anything you might say or do, I am already doubting my own professional self-worth. I have to fight the lies every day, and remind myself that the work I'm doing has a significant impact on the people I serve. I have to remind myself that writing touches lives in a way that is beautiful, and profoundly mysterious. It is a constant, uphill battle.  

As hard as it is to admit, your requests for me to ditch work for a few hours, or hop on an airplane and leave for a few days aren't helping. These requests imply, however unintentionally, that my job isn't a real job, and that it isn't as valid or valuable as someone else's. I can pick up and leave whenever I want. Yes, it is technically true that there is flexibility in my situation. But is it right to stop working whenever I want, just because I technically can? Isn't it good to pursue work that matters, to commit myself professionally, to hold myself to a certain number of work days each year like everyone else? 

This leads me right into my third point. 

3. I am at the top of everyone's daytime help list.

This is absolutely the hardest point for me to share with you, because I don't want you to get the wrong idea. I WANT TO HELP! I hope you'll keep that in mind as I explain.

I get a constant stream of completely legitimate requests for my time, ranging from a couple of hours to a full day. I am at the top of everyone's list, because I am flexible, technically available most of the time, and I don't have young children at home.

These requests span a variety of needs:

  • Babysitting
  • Rides to the airport
  • Hanging out at your house to meet contractors or deliveries
  • Dropping you off at the auto shop, then taking you home, then bringing you back later
  • Providing emotional support on a hard day

Well-meaning friends often ask me for my time during the day, frequently for a commitment spanning half a day of work including travel time. As I mentioned above, the hardest part is that I WANT TO HELP! The requests are coming from you, after all--a friend, a loved one, someone I desire to support and serve. But I also have a job, and these requests do--however unintentionally--imply that my work is less important than your current need. Where do I draw the line? At what point do I say 'no' to protect my professional self-worth, and when do I set my work aside to serve others? 

This is a balancing act that I have yet to master. I have no idea how to get it down to a system without feeling like a selfish jerk most of the time. But for now, until I figure it out, I practice saying 'no' a lot. I say 'no' because I get too many of these requests, and I just can't manage them all. I say 'no' because routine is vital, and professional self-worth is a daily challenge. You may see a massive blank-spot in my schedule because I'm not accountable to a traditional supervisor, but that isn't the case. I'm accountable to myself, and to my work, just as much as anyone else is. My husband goes to an office every day and works his tail off so that I can stay home and do what I love. I have a responsibility to him, too, to honor his sacrifice and not waste the opportunity he gives me every day.

The best advice I can give you is to be specific--give me all of the details when you ask for my help, including the specific time range, why you need help, and what you expect of me. In the case of an emergency or extenuating circumstance, I'm more likely to say yes. But you have to tell me that's the case in order for me to know. I am not a mind reader, and I cannot meet every need that comes my way. 

Don't stop asking for help because you've read this, but don't assume I'll say yes because I work from home, either. Identify some other people to rotate through when you have a daytime, weekday need. Maybe acknowledge that my work matters, and that you realize you're asking me to give up something more than just time.

Above all, know that I care about you and your families, even when I say 'no.'

4. Success isn't measured by annual salary.

On occasion, people literally laugh when I tell them what I do. Others are more subtle in their disapproval and skepticism. I've had people follow up with, "Are you successful?" This is code for "But do you make money, and if so, how much?" I mean, think about that for a second! Imagine meeting someone at a cocktail party. You ask what she does, and she says she's an accountant. Is your follow-up going to be "Okay, but how much money do you make?" How do you think that would feel, on her end? Would you consider that approach to be polite, or respectful of her as a professional?

I know that many people don't understand the reality of creative work, or the value of it at all. I understand that many people are accustomed to working a 9-5, getting a regular paycheck with benefits, and having a certain number of PTO days. Everything is neat, orderly, and data-centric. My work is admittedly different, but that does not make it less valuable. There is no valid reason to be suspicious or disapproving of my profession as a creative. 

It all comes down to how we, as a culture, define and measure success. If you measure success by your paycheck, I'm so, so sorry. That is a narrow, shallow definition of success that leaves your professional self-worth and success dependent on the economic success of your employer. Instead, I try to define success more broadly--by the impact that I have on individual lives with my clients, and the future impact of the stories I write. I measure hours, effort, client satisfaction, and words on the page. 

You may not believe me to be successful--fair enough. But I would ask that you consider why you feel that way. What is it that makes you so determined to measure someone's professional value in dollar signs? What truths do you believe about yourself, about the people around you? I invite you to explore your own perception of identity, and at the very least, to assume the best when you do not understand someone else's job. Ask questions, and be curious. 

5. My work is just as challenging as yours, every day. 

Though the schedule and individual components are radically different, self-employment is just as challenging as a 9-5. These challenges are consistently present, and they are 100% real. 

Here's a quick summary of my greatest professional challenges, with some reiterations of the points above:

Doing my job every day, even though nobody is making me do it. When I'm tired, getting up early with no external accountability or appointments. Putting words on the page every day, even though I might never sell a book. 

Saying 'no' to laundry and errands, and 'yes' to my work. Sticking to a schedule, because my work is valuable. Saying 'no' to friends during the day, because eventually I have to get something done. Working a full day, even if my husband comes home early from work.

Being alone most of the time, especially during the winter. Managing Seasonal Affective Disorder with the realities of working from home. Finding ways to be social and counter loneliness, without dramatically sacrificing my work time. 

Creative Energy
Understanding the realities of creative work, and how that energy is best fostered. Giving my creative mind what it needs in order to succeed. Being satisfied with 3 hours of creative work, because it takes a lot of fuel to make it happen. Balancing the reality of creativity with my desire to get a project done. Being patient as I learn to understand my creative self.

Refusing to believe that I am defined by dollar signs. Daily affirming that my work is valuable, no matter what the world says. Charging a fair rate for my coaching services, and having the guts to charge friends or family members. 

Inconsistent Work Flow
Managing busy seasons of multiple clients, and adjusting to slower seasons. Identifying new clients, and maintaining a routine despite seasonal fluctuations. Setting goals when I can't predict how many clients I'll actually have. Budgeting for an unknown amount of work. 

This is not an exhaustive list, of course. There are challenges I'm not even aware of, or items I've forgotten to mention. The point isn't the specifics of each challenge, even--it's the fact that these challenges exist, and that they are significant. I'm not lazy, and I'm not sitting at home every day watching Netflix, even though I'm regularly tempted and able to do so. 

My work is not a playground. Yes, my work is fun, and I love what I do! But it's still work, and it's still broken, just like more traditional jobs. 


I hope these points are illuminating for you. I hope you learned something, and that you came away with an understanding of self-employment that you didn't have previously. That said, this is absolutely not universally applicable to every self-employed person in the world! Don't assume that my perspective is the same as someone's else's. Instead, ask questions, get to know your self-employed friends, and challenge your own assumptions about their work.

Above all, let your self-employed friends--especially the creatives--know how much you value their work. Remind them know that their work matters, and that it's freaking awesome that they get to pursue something like fiction, photography, or dance. We need to hear it. We need to know that there are people out there who don't think we're foolish dreamers, wasting time and wasting space. 

We need people who are willing to read this blog post all the way through, who care enough to ask questions. Thanks for making it this far, my friend! If you have any follow-up thoughts or concerns, let me know in the comments below, or reach out directly

Recent Read: The Deed of Paksennarion by Elizabeth Moon

Read on without fear, my friends! Recent Read reviews do not contain spoilers unless otherwise indicated in big, bold, impossible-to-miss fonts. 

A few weeks ago, I offered my thoughts on the first installment of this trilogy by Elizabeth Moon. Typically, I would wait to review a series until I finished the final book, but in this case, I was in a low period of productivity and inspiration, and thus wildly reaching for anything and everything I could feasibly write about. Mercifully, life is starting to swing back toward normal, and I'm off to a good start this week. I mean, it's only Tuesday, and I'm already blogging! Huzzah!  

If you've read that initial review from a few weeks ago of book one, titled Sheepfarmer's Daughter, you know that this is an epic fantasy trilogy written by a woman, about a woman--this was my main reason for diving into the story. Prior to a couple of months ago, I'd never heard of this series, or of Elizabeth Moon. Andrew ran across the series title in an article somewhere, and it was being held up as one of the great epic fantasy triumphs, alongside Tolkien and Rothfuss. 

Hunting down this series can be a bit confusing--originally, the story was published as three separate (and much more digestable) volumes in 1988 and 1989: Sheepfarmer's DaughterDivided Allegiance, and Oath of Gold. In the late 1990s, Baen published a combined version of the series, titled The Deed of Paksennarion. This gargantuan compiled version is the one most readily available in our local library systems, and thus might be the best place to start if you go hunting for the series. 


As I mentioned in my initial review, the first book was slow, cumbersome, and too distant for my taste. The level of world-building detail was astonishing, and an obvious nod to Tolkien, but I felt too removed from the characters, including our title heroine Paksennarion--Paks for short. 

Friends, this is somewhat embarrassing, but I have to give it to you straight: my initial impression could not have been more wrong about the series as a whole. 

Now that I have read the entirety of The Deed of Paksennarion (three books often presented together in one published volume), I can say that it is a brilliant and worthy addition to the classic rockstars of the epic fantasy genre. Moon creates a world clearly inspired by Middle Earth, but also entirely distinct. And in her heroine, Moon develops a fresh and surprisingly complex woman, a heroine worthy of the reader's admiration and respect.

If you're a regular on my blog, you can imagine what a fantastic surprise this was for me. I have been tremendously disappointed with the garbage heroines being written--by women--especially in modern young adult speculative fiction. This comic by author and illustrator Adam Ellis sums it up nicely:

Credit  Adam Ellis , @adamtots. 

Credit Adam Ellis, @adamtots. 

In addition to Adam's observations about young adult heroines, I would add that they tend to be bitter, vengeful, violent, and romance-obsessed. Anger is lifted up as their most redeeming quality, and ironically, this makes me want to punch some people in the face. Is this what we want to promote in our culture, and for our young women? Do we really want our friends and nieces and daughters to admire these heroines who are obnoxiously broody and selfish? 

This is one of my primary goals as an author--to write flawed heroines who can still be admired and respected for the right reasons: heroines who inspire young women to be brave, kind, independent, intelligent, and thoughtful. 

So you can imagine my delight when I got deep into Paksennarion's story, and completely fell in love with her. Is she my ideal heroine? No. Her behavior is more passive and meek than I might hope to promote in my own work, but even so, one could argue that her choices are context-appropriate, and the best decisions she could make in the world that she lives in. 

One particularly compelling aspect of Moon's story is spirituality, and the interaction between various characters and the gods they choose to serve. Paks' journey is certainly spiritual, and takes her to a place of open-handed obedience and faith in her path and decisions. This, in my opinion, is a woman worth admiring--a woman whose faith leads her to do good, who acts according to the leading of her god, and who does not respond with selfish ambition, but instead with selfless sacrifice and tireless commitment to do what is right. 

My only surviving complaint from my initial impressions is that the character development for secondary characters is so sparse. There are many, many characters that Paks encounters on her journey, and they are given very little attention in the way of development. Even Moon, whose character development is so subtle and effective, has left me feeling that I don't really know many of those characters beyond Paks. By the end of the series, I still had trouble visualizing other characters and keeping their names straight. But perhaps this was intentional--perhaps the reader is meant to feel the fleeting moments with these individuals as Paks walks a lonely road. Regardless of intent, this left me feeling a little cheated as a reader, and hungry for more information.

That said, The Deed of Paksennarion is a magnificent, fresh take on an epic fantasy, centered on a well-developed heroine. Paks' journey feels new and unusual because she is so different from the women who are elevated in our culture. If you are looking for a surprising and patient read, I strongly recommend picking up this series.

Path to Writing

Looking back, I find it completely hilarious that I never saw writing coming. It has been sneaking up on me for years, and in my typical unobservant fashion, I had no idea. Completely, 100% oblivious.

Growing up, I was absolutely a reader. I devoured scads of books in record time. Late into the night, my parents would often find me on my bedroom floor with a box of Club crackers, a package of pepperoni, and my nose in a book. I couldn’t stop, and quite frankly, I didn’t want to. I read through meals, and periodically in the car on longer road trips, though it made me nauseous to do so.

Specifically, I was a delighted reader of fantasy. I was a proud member of the blessed generation that was the same age as Harry with each book release. Hermione was my homegirl...she understood me. At every opportunity, I hungered to be whisked away to another world, more magnificent and adventurous than my own.

I wept and rejoiced with my fictional friends, but never really thought of creating fictional stories myself. There was a brief period where I snuck my parents’ typewriter into my room and made up some two-page stories. The feel and sound of the keys was divine, but I struggled to come up with content. Frequently, I ended up with an unfinished and unsatisfying tale about an encounter with a cute boy at summer camp.

My first journal entry is dated October 12, 1998, which puts me around 10 years old. The diary itself is about 4”x4”, glossy white covered with rainbow colored hearts, and capped with a little gold lock and release button. I handle it with fondness even now, though the content is absurd. And I always hated the word ‘diary’ -- it was too frilly for my purposes. I took journaling very seriously. Which is pretty ironic, considering the rainbow hearts.

I have upwards of 20 journals spanning 1998-2016. Though the habit has died out a bit, writing has never ceased to be a cathartic and necessary part of my life. The format and content have gone through countless iterations: Xanga poems about middle school crushes; a blog about the challenges of being 15; notebooks full of song lyrics; another blog about restaurant and recipe critiques; thoughts on my experiences, fears, pain, joy, dating life, trauma, disappointments, and spirituality.

But all of this was happening in patches of spare time, while I focused on the “really important stuff.” I got a bachelor’s degree in music after studying to be a high school choir teacher for 3.25 years…a terrible, hilariously ill-suited career choice. Graduating with honors, finding Mr. Right, and figuring out how to pay my bills were my absolute top priorities.

Then came depression, hopelessness, and a bittersweet end-of-the-rope experience that led me to Jesus. I won’t tell that story today. I doubt that I’ll ever be able to do it justice when I do.

Even then, armed with a better foundation for my identity and purpose, I flailed when it came to career direction. In the five year period following my undergrad studies, I held the following positions, most of them full-time:

  • Assistant Manager at a rock climbing gym
  • Sales Specialist at Apple
  • Executive Assistant to the General Director at an opera company
  • Admission Counselor at my alma mater
  • Director of Operations at a non-denominational church
  • Search Associate for an executive search and strategic planning consultant company

From 2014-2016, I had four separate careers. When I say that I “flailed” professionally, I am not exaggerating. I had no idea what I was meant to do with myself. I have always excelled in the broad base of skills one needs to succeed in the 9-5 world. My performance reviews were always sky high, yet I felt like a prisoner every time I tried to make that sort of traditional career “fit”. I took every career and personality assessment on the market, and time and time again, the professional involved would say, “Hannah, you just won’t be content until you work for yourself, or have a significant amount of freedom.”

“That’s super!” said Hannah at 23. “But I have bills to pay. So I’m keeping my 9-5 in the nonprofit sector because I can get behind the cause. I’m working toward something meaningful. I’ll be just fine.”

I was never fine. I lied to myself over and over again, and was bored out of my mind. I cried in the bathroom at work and wondered what was wrong with me. Why couldn’t I just suck it up and do my job like everyone else seemed to be doing?

I got engaged to my best friend and the best man I know in December 2014. I made a transition to working for the church, and he was also pursuing work in full-time ministry. I was elated. We were on an energizing, joyful path, and I couldn’t be happier.

That season leading up to our engagement was the closest I had ever come to professional contentment. When I was working for the church, I had a lot of flexibility in my schedule, I was treated as an equal even with my lack of experience, and I was surrounded by wonderful people. True to God’s nature, though, he had better plans. So havoc wrecked my world for the next 18 months.

In the time leading up to and following our wedding and honeymoon in September 2015, all hell broke loose. I am not exaggerating. One church leader called it “the perfect storm of awful communication, timing, and circumstances,” among other things. We have many colorful names for that particular season of life.

I lost my roommate and was having anxiety attacks. As a result, I moved once, and then again after six weeks. An important relationship in my life turned destructive, and I endured months of manipulation and psychological abuse. As a result, I was later diagnosed with complex PTSD. With no alternative employment, I left my job at the church, and Andrew left seminary to pursue his original line of work in the business world. We had no income. I quickly took on a job to pay the bills, but my PTSD symptoms made it impossible for me to continue on in that position. It just wasn’t the right fit, and I wasn’t ready to work. Full of shame and self-defeat, I resigned after four months. Andrew’s job search continued for an additional four months.

Needless to say, it was an exhausting season. There was a lot of crying, and a lot of Netflix. And fortunately, there was a lot of support and encouragement from our wonderful family and friends. Perhaps most fortunately, our marriage survived the madness. We joked often about writing a marriage book years from now, based on the absurdity of our first year and what we learned from it. Perhaps we’ll do that, someday.

In addition to vegging and binging our favorite TV shows, there was also a lot of reading in that season. The local library was suddenly a paradise of entertainment as a household with no income. I think I read the entire Dresden Files series in something like four weeks. We read the existing Way of Kings books, and many, many others.

On September 2, 2016, we sat on a picnic blanket in Lafayette Square watching one of the annual Gateway Cup cycling races. (Bless you St. Louis, and your abundant, free events!) It was a beautiful evening, and we were having a lovely date night. Andrew was quiet, as he often is, and then mused, “What would you write about if you could write a fantasy story? What would your magic look like?”  

It would be dramatic and wonderful if my response had been “Eureka! That’s it!”, but it really was more of a slow realization. A revelation that became more exposed by the millimeter, melting warmth and light over my life like a sunrise.

Our conversation continued for the rest of the evening, considering possible systems of magic, character backgrounds, possible underlying themes. And the conversation hasn’t really stopped since.

I’ve never been so thoroughly and pervasively eager to make something a reality. I bought a notebook 3 days after our date, and went to the library more times in those first few months than in the previous 5 years combined. As I always have, I devoured books on writing speculative fiction, and a number of prominent books in the field of fantasy and science fiction. I created my first system of magic for my first project, axed that system, and replaced it with a better one.

I spent 3 months brainstorming, researching, developing characters, and outlining plot. Then I wrote my First 350 Words. The project continued to grow into something surprising and wonderful, and it was a delight to wake up and make a story unfold every day. I finished my first draft of my first book on March 15, about 6 months after that first lightbulb moment. Subsequent (and more marketable) projects have developed since, which I continue to pursue daily, and I love it.

Not to say that it isn’t daunting. It’s daunting as hell. Initially, the writing process was literally just thousands and thousands of questions:

Who is my heroine? How old is she? What does she look like? What are her relationships like? How does she view herself?

Well, that depends…

Where does she live? What is her culture’s world view? What is the landscape like? What resources do they have? How does that affect trade? Is her region part of a larger world? Where is this world? Does it follow the rules of Earth?

What does magic do in this world? What can it do? What can it not do? How is it limited? What happens if you try to use it the wrong way? What fuels it? What is its origin? Has it existed in time before this story? Who can use it? How do they learn to use it? How do non-magical people respond to it?

And on, and on, and on, and on, and on it goes.

So yes, it’s daunting. And normally the lazy person in me would throw up her hands and say “Ugh, whatever! I’m taking a nap.” But I can’t get enough of the writing process. It feels as if the words are a part of my flesh… a subconscious biological process like breathing, and my body doesn’t consider stopping.

Thanks to these moments along my journey, I can say that I’m here today. I’m an author; I’m a writer. I haven’t been published, but I thrive on writing. I embrace the thrilling opportunity to craft a reader’s experience through fictional stories. I hope to have the opportunity to share those stories with you someday.

Do something you love today, friends. And whatever that may be, embrace the experience as the extraordinary gift that it is.