Any advice on how to stay motivated?​

Questionable Advice

Questionable Advice #10: Any advice on how to stay motivated?

Hello Kara,

My name is Kaitlyn, and I am emailing you just because I am beyond inspired, impressed, appreciative, and many other things with your work on your website. I relate to this work so much in terms of my aspirations and passions after I graduate college. 

I stumbled upon it because I have a cool professor who is having us do an independent research/experiential project on something of interest to us. Mine was emotional intelligence and self-awareness (how to build it in yourself and in organizations, why it matters, the benefits, everything). So it was a completely random Google search that led me here.

What I wanted out of this email was just to say:

1. GOOD JOB with all this work you’ve put into your blog. It speaks to me beyond what you know!

2. I have been thinking a lot about starting my own blog, book, podcast, or something on similar topics you’ve been sharing. I am curious how you went about doing this because you are literally what I want to be! Any advice or takeaways from your personal journey to develop this site and stay motivated to put so many hours into it would be awesome.

Best wishes,


Hi Kaitlyn,

I almost sent you a quick reply, because I’ve been truly terrible at replying promptly this year. But then I decided to use your email as a reason to reflect on my personal journey. So really, I should be thanking you for the inspiration and encouragement. I should probably also be apologizing for the length of this response, and how much I made it about me. But I hope you’re able to glean something from my long reply (and I did put “What I Learned” and Personalized Questions at the end). As you read my story, I encourage you to use it as a prompt for reflection. Think about how the experience and crossroads might apply to you, and what you would do in those situations.

Again, thank you for reaching out–it really does keep me motivated to keep doing what I’m doing. I welcome any further questions or feedback you may have, and I promise I can be more specific if you have future questions about specific topics related to the online world.




I got further than most kids with my dream of being a published author. Not in the actual publishing sense, unfortunately, but in the sense that I wrote several books, queried literary agents, and even had one request to read the manuscript. You have a strong narrative voice, he said, but unfortunately, I have to pass. And with his words, my last hopes at becoming the next S.E. Hinton––teenage writer extraordinaire––quietly dissolved.

I’d be remiss, however, if I blamed him for the deterioration of perseverance with my writing goals. That particular element had been crumbling for years. As a teenager, I blamed my involvement with sports for the reason my writing was neglected. (I still remember a dramatic letter to my father which cited: Why is it that my writing, which has never caused me the emotional pain like basketball has, gets neglected in my room?) And then in college, when given the chance to propose a writing project for my Creative Writing senior thesis, I chose to write about my experience playing a college sport–because it let me focus on basketball.

It was only years later that I came to admit that nothing forced me to neglect my writing. I chose to prioritize things over writing. I became a teacher and coach. I developed a workout-obsessed eating disorder. I filled my time off with travel and summer jobs and social plans.

And–as with many of us–my ever-present “life” got in the way.

I did continue to write in the first two years after college, and even completed a 150-page book. But, unbeknownst to me at the time, the perseverance needed to be a writer was gone. Sure, I had the discipline to sit down and force myself to put words on the page if it was a goal (and if it fit behind my other front-facing, work-related goals). But I didn’t have the perseverance to sit down and sit with the words like good writing demanded. 

As I stood up in front of my high school English class each day and empathetically told them the importance of revision, I shriveled at the notion of reworking what I had “finished” writing. The idea of not being able to check “done” on the writing to-do list sent me spiraling toward other things.

Naturally, the feedback I received for my 150-page book required substantial revision. And it never saw it.  

After a couple of years, however, I felt that dormant desire to write stirring again. This time, I understood myself better. I was aware that, for many reasons, I wasn’t in a place to embrace a large project. I also knew that if I didn’t hold myself accountable, I would slip right back into the familiar cycle of prioritizing everything else above writing (a.k.a. human nature at its finest).

So I started a hobby blog to tap back into my passion for writing. I paid $70 for a year-long domain name (enough money to make me feel compelled to not give up, as I hate wasting money). Airplane Windows and Bathroom Mirrors was born: a blog that traveled outward and inward.

Blogging, as it turned out, fit nicely into my skill set. I could write quick, snappy posts, and then feel the satisfaction of checking them off my to-do list (very little revision required). I had the organizational skills to juggle the different tasks: writing, website design, research, and outreach. And, unlike the perseverance needed for long-term writing projects, my discipline served me well in tackling the many smaller tasks required for blogging.

I began to wonder if I could still realize my dream to be a professional writer, just in a different avenue. I attended a travel blogging conference to see if blogging still inspired me; and if it did, how I should proceed.

The conference presented me with a crucial decision: I could continue to write a weekly post for fun, or I could amp up my pursuits to gain a real audience.

Inspired mostly by my long-held desire to be a professional writer, and partly by my unhealthy need to attach external worth to my pursuits, I chose the latter. I amped up my endeavor in nearly every way: money invested, time invested, research hours, social media presence. I changed my domain name to My Question Life, inspired by the flexibility yet focus it could give me. 

I like to call this stage of my blog MyQuestionLife 1.0.

I wrote more posts, but this time they focused on narrower themes; teaching, female empowerment, and travel – all my passions. The website design took hours, and every time I figured something out seemed to lead to a new obstacle. (I still harbor a pervasive loathing of all things WordPress–something that pushes me closest to quitting, and something I’m attempting to reframe my mindset around.)

I also took the most difficult step of it all: I shared the blog on my social media. It took all my courage to send the post, and it triggered what felt like all my vulnerability in the anxious avoidance that followed. I had no problem telling my best friends; likewise, sharing the blog to strangers was easy. However, the terrifyingly wide net of people between the two is who haunted my imagination and filled my ears with hypothetical judgment. You know the group, filled with those acquaintances, work colleagues, and past relationships that you clearly remember and vaguely wonder what they’re up to.

The outreach felt doubly vulnerable because it wasn’t just sharing my stories (which often contained personal anecdotes). It was sharing my dream. My belief that I could “make it as a blogger.” Writing this now, I still hear an unassigned voice saying, I can’t believe she thinks her writing is good enough for that. 

As you might expect, the actual responses I got were much more positive. Some of those haunting faces–the ones I worried most about, for whatever reason–even reached out in support. And, you know what? Most people didn’t respond, or reach out, or even care. 

That’s the thing about vulnerability. When something feels so important to us, we tend to assume that everyone else cares just as much. And, to be quite frank, we’re just not that special–despite our fanciful fears making us believe otherwise.

Once my blog–and my dream– had been put into the world, I could get down to work again. This time, the work came in the form of figuring out how the heck to make a blog successful. 

Turns out, a successful blog can mean a lot of things. However, the one universal necessity I understood from day one was that I needed traffic. Without readers, it was just me paying to put my words into the Internet world (a reality that I have considered enough to fulfill me).

Despite my best efforts, MyQuestionLife 1.0 wasn’t yielding the results I wanted. So, a couple months later, I dove back into blogging research again. This time I didn’t overlook the information I thought I could bypass in the first place (aka Search Engine Optimization, catchy titles, specific themes, branding). You know…all the parts of our passions that completely suck but nobody likes to acknowledge. Writer Mark Manson calls this your “flavor of shit sandwich”.

I ate said shit sandwich, and MyQuestionLife 2.0 was born.

I also adopted the driving goal that all public content producers must hold: my writing had to be for others, not for me. Sure, my anecdote about getting into an argument with my partner felt therapeutic to write about. But did it offer the reader something? Did I include it as a means to an end, rather than an end with the hope that there was some means? (Also, I feel the irony in saying this as I write a lengthy personal narrative. But at least I warned you!)

Several other crossroads emerged, as well, that I had to make a choice about. The first was the quality of writing. Blog writing didn’t require deep contemplation and honed writing skills. I quickly came to realize this in my research and perusing of blogs I found on Pinterest.  On the contrary, many of the most successful blog posts lacked strong writing. List-formats and dramatic titles reigned as leaders; posts populated with keyword-stuffed headlines emerged as champions. 

How far from my original goal–to rededicate myself to writing–was I willing to go? Did writing in any capacity, regardless of its creativity or heart, still fulfill me?

The second crossroads set me in front of a central human dilemma: profit versus experience. As I learned more about how to make money on the internet (and as I learned how many blogs make money off instructing people how to make money), I understood that my actions required me to make certain decisions that I hadn’t anticipated.

How much was I willing to change in order to make my blog marketable? What marketing tricks did I feel comfortable using to tap into human behavior? And what would take precedent when I made decisions–my readers, or my profits? (Mind you, even deciding to prioritize profits didn’t mean that they came. I still had very little clue on how I could make real money.)

Both these junctions–writing quality and money-making ethics– found me in regular attendance over the last four years, and I still frequent them today. Not surprisingly, I’ve found that their questions don’t yield black and white answers. Instead, it’s a swinging pendulum that you’ve got to find a balance within. And it’s a trial-and-error process as you swing.

For most of the years, I managed to keep some whisper in my head that said, “Don’t stop.” Even when I spent hours writing and designing an Ebook that didn’t make me any money. Even after I spent $10, then $15, then $20 a month on my email subscriber service, despite the fact that I often neglected it and never used it as many other bloggers did: as a funnel source to make money back. 

And even after planning a wedding and starting a new, all-consuming job, when my mental bandwidth became so full I found myself crying on the kitchen floor, and had barely looked at my blog in five months, and faced the very present question: should I just give up on it?

Even then, something from within told me that no, it wasn’t time yet. For reasons unknown to me, but also reasons I had to accept might never fully reveal themselves.

I think that’s what creative content dreams like this require. Simultaneously holding onto the exciting possibilities of “what could be” while letting go of our personal expectations for “what could be.” The fine dance between imagination and acceptance, anticipation and contentment, an unrelenting pursuit and a relentless openness to change.

It also requires a constant self-inventory of oneself.

The first time I saw my blog post land itself on Google’s first search page brought tears to my eyes. When my “Free Self-Awareness Test” landed in the #1 ranking spot, I felt immense satisfaction and pride in my work. That #1 spot came through hours learning about SEO keywords, creating a strategy around my blog’s theme, and endless outreach via email to try to secure backlinks. It’s difficult to stay motivated without seeing results.

But prioritizing keywords and backlinks wasn’t why I started blogging, and something was missing. I needed to find ways to balance this non-writing work. I challenged myself to include narrative writing within my list-themed posts, and over time, I think it’s strengthened my writing. I also started the “Questionable Advice” section, despite it adding no Google-traffic-driving value to my blog. 

I found that, as much as I did these things for my readers, I also did them for me. And I came to realize that this distinction was not only okay, but necessary for me to stay inspired in my work. I could play the money-making, market-requiring games so long as I protected some space for the original “why” behind why I wanted to start a blog.

I also found creative ways to bring in my other primary value–connection–that seemed to be missing when my readers existed only as statistics on Google Console. Using my blog as the jumping ground, I reached out to authors and other creatives asking if I could interview them. These interviews turned into blog posts (some based on keywords, others that didn’t), but more importantly, they turned into a sense of connection through MyQuestionLife that had been lacking before.

As I look back, I believe reflecting on where my values–curiosity, connection, creativity–fit into my blogging benefited my blog and my life. It taught me to pause and ask, Do I see my values in this endeavor? If not, is it something that fulfills me? If I want it to fulfill me, how can I incorporate my values more?  

Now I approach every major decision in my life by asking these questions. I’m not always correct, but the outcome can still be powerful.

As for profits, I wish I had more insight to offer on how to turn this love of mine into a full-time job. It’s easy to get sucked into the income reports and success stories that rank on “how to make a living off of blogging/podcasting/etc.” But the truth is, for every successful blog, there are thousands that didn’t figure it out or take the time to get there.

Because of my work for MyQuestionLife, I stumbled upon a freelancing opportunity with a passionate and successful website creator. This work earned me my first real paycheck, and despite the fact that it wasn’t my blog that directly earned it, I appreciated that MyQuestionLife still yielded the opportunity.

As for my website, I avoided ads for years, saying that they would hurt “the integrity of my blog.” I loved how clean and crisp my posts looked with flashing texts and random pop-up windows interrupting the intentionally crafted paragraphs. Over the years, I became satisfied with the fact that my own personal investments in time and money were worth it for the joy I gained from the overall experience. 

However, after a failed Ebook sales attempt, a less-than-profitable online course venture, and an abysmal profit margin on affiliate links, I began to ask: do I want my years of hard work to yield some profit?

Again, I had to wrestle with myself and my values. I also had to trust that my answer today didn’t need to be the same as my answer tomorrow.

During the five months I neglected my blog, an ad salesman reached out to me. Struggling to find time to actively gain purpose from my blog, I figured I might as well try to passively gain profits. So I responded, and thus, MyQuestionLife 3.0 came into fruition. Less pretty, more distracting, but more profitable.

I’m nowhere close to making a full-time income on my blog. And I think this ability to make choices without feeling the pressure of needing an income has helped me greatly in terms of clarity and enjoyment. (In the book Originals by Adam Grant, he spends a chapter discussing how the “starving artist” is actually detrimental to creative success. I encourage you to read it). I also haven’t let go of the dream of making enough income off of my blog and creative endeavors to have it be my full-time gig. 

But for now, I’m happy with the current decisions at the two crossroads–writing and profits–that I’ve made. Ask me in a year, and my perspective might be different.

That’s the biggest lesson I’ve taken away from my blogging pursuits: that no matter how much planning or research you do, you’re never going to reach the final iteration. There is no MyQuestionLife Final #.0 version. Every version held its own worth, every version taught me something, and every version got me to this current version. 

At times, my motivation skyrocketed, but it came from outdated beliefs I had rather than true values. Other times, my clarity was crystal clear, but my motivation ebbed. I’ve spent hundreds of dollars without seeing any monetary payoff, but somehow–at times–understood that the purpose it gave me was worth it. Two months ago, I received my first ad paycheck–about $1,000–and taped it to my wall because I felt so proud.

For periods of time, I looked at stats that told me 800-1,000 people visited my blog every day, but the little graph on my phone didn’t hold any real weight for me. Then, I would remind myself that those numbers represented real people, and I’d feel immense satisfaction in the fact that I was helping people. Every once in a while, I would get an email from someone sharing their vulnerability with me in such a powerful way that made me think, If my blog helped this one person, then it was all worth it. 

In the last four years, I nearly threw my computer out of the window when trying to figure out javascript and WordPress. I spent hours learning and developing my blog’s Pinterest, only to have a glitch erase months’ worth of progress (a struggle that still makes me too tired to think about restarting). I wrote an entire Ebook, turned it into an entire online course, and quickly realized that my entire premise–trying to convince people who weren’t self-aware to be self-aware enough to invest in their self-awareness–was flawed. Turns out, I should’ve put a bit more thought into the business side of things before starting.

That being said, I have learned a ton about business, marketing, and a handful of other topics. Throughout the never-ending research and application of that research, I’ve also learned where to thread my passions into the less-than-exciting blogging strategy. The entire process has reinforced my aptitude for learning, and in doing so, I’ve become an expert on things I never anticipated when starting out. 

Off of WordPress, opportunities have indirectly emerged from my blog that I never expected. New ideas, connections with awesome people, and even career changes. The phrase, “Energy flows where attention goes’ contains powerful truths when you put yourself into the world and open yourself to possibilities. I credit my recent job shift from teaching to communications in part to my blogging ventures; I even feel at peace that if MyQuestionLife’s main purpose was to get me to where I am in my career, then that was an honorable purpose indeed.

I’ve cried tears of joy, frustration, and anger. I’ve felt what feels like every shade of vulnerability throughout this journey, and yet I’m sure next week I’ll feel a new one.  I’ve felt anger and hurt when the most important people in my life didn’t read my blog posts, but it taught me to name the support I need and ask for it from the people I trust. I’ve also learned to appreciate that encouragement can come from surprising people and places. And I’ve developed a sense of confidence in myself and my work that I never thought I would’ve when starting out. 

I share these specific things not because I think my story is incredibly unique or inspiring. Instead, I write these things because it’s their mundandenous that makes them powerful. The honest, candid, and sometimes boring aspects that become hidden in the online world of catchy titles, keyword-targeted formulas, and look-how-successful-I-can-make-you stories.

What motivates me to do what I do? 

Honestly, I can’t answer that. My answer changes all the time. But I think it’s the beauty of this evolution that keeps me going. The purpose in having a creative outlet to better understand myself and my place in the world.

My advice to you Kaylin, is to go for it, whatever it is. You might find that you’ll discover what you’re looking for along the way.

Lessons I’ve Learned

  1. I learned that, no matter how much research I do, I can’t know everything about what makes a blog successful before I start something. There’s too much information to absorb all at once. As I try to implement the different strategies, it’ll always come back to a process of trial, error, and–lookatmenow–reflection.
  2. I learned how scary it feels to put your dream into the world and have to publicly acknowledge it. I think anytime we have to tell others, “This is something I really care about and want,” it’s inevitable we hear a chorus of imagined replies in our mind: “It’s a stupid dream.”
  3. I learned how to keep these voices at bay, at least so they don’t get in my way. Don’t get me wrong–sometimes they can be extremely loud. During those particularly vulnerable moments, I go back to my defenses: reminding myself why I’m doing it, tapping into the joy I feel, reading my favorite authors, and talking to my people.
  4. I’ve learned that sometimes you just need to do. You can’t be prepared for everything, and sometimes taking the first step–even if it’s the wrong one–will still get you moving toward the direction you want to go.
  5. I learned that it’s okay to feel the desire to give up, and it’s even okay to give up on something–but only if you’re doing it to make space for something that’s more in line with what you want.
  6. I learned that you have to name your values and then continually come back to them on your journey. Ask yourself: Do I see my values in this endeavor? If not, is it something that fulfills me? If I want it to fulfill me, how can I incorporate my values more?  
  7. I learned that my values and what they look like can change. What I believed yesterday might be different today, and it’s okay to let go of old expectations to make room for the new.
  8. I learned to draw lines for myself on what I feel morally good about doing with my blog and for my readers. We all have different moral lines, but it’s when we don’t realize them or see how they’re playing out that things get messy.
  9. I learned how to reframe success and define purpose for myself. This requires a lot of internal reflection, despite the fact that our natural default is to look outward and compare.
  10. I learned to be patient with myself. Everything takes longer than I initially thought. I failed to meet most of the deadlines I set for myself, which is not an easy thing for me to do. It also forced me to reflect on the deadlines I do set and if they’re healthy and realistic.
  11. I learned that I can’t rely on anybody else to encourage me forward. I have a small circle of people who support me wholeheartedly, but they have lives and their own pursuits, and my blog is not at the forefront of their minds (nor would I expect it to be). 
  12. I learned to identify what I do need to feel supported by my relationships, and how to express that to them. 
  13. I’ve learned more about my strengths, as well as the limitations that come on the other side of those strengths. I’ve also learned to investigate my mindset more closely, because some outdated beliefs might no longer be serving me.
  14. I learned that the phrase “Everything happens for a reason” is more of an attitude than a belief. It’s up to us to look for what experiences give us, and then use those findings to inform how we can live our purpose moving forward.
  15. I learned that emails from people like you can prompt me to write eight pages worth of reflection–the longest piece I’ve written in a while–and inspire me to realize I still find purpose in this pursuit. For that, I thank you immensely.

Personal Questions for you:

  • What are your core values?
  • How will your values fit into your creative work?
  • What about starting a creative pursuit (blog, podcast, book, etc). most excites you?
  • What do you hope to gain from starting a creative pursuit? Are you open to allowing this to change?
  • How do you define success and failure? How much is this definition influenced by others versus yourself?
  • Even if nobody read or listened to your creative pursuit, would you still enjoy creating it?
  • How often do you check-in with yourself on your dreams and aspirations?
  • How self-aware are you when it comes to your emotions?
  • What are some of your strengths that will help you with your creative pursuit? What are the things that will hold you back?
  • How can you find a way to start your creative pursuit without putting too much pressure on it (and sustain your bills in the process)?