Digital Nomad Tricks: Building a Plane While Also Flying It

Where I Am

I come bearing good news: I’m in a much better place professionally than I was when I wrote my last entry (yay!). I’ve been hustling non-stop since early February, which has translated into me securing a 6-month long contract with a new client, as well as another smaller contract that I believe will help me generate some supplemental income for the next few weeks. I’m also in the middle of interviewing for a position to work part-time as an Editor for a niche website, which is super exciting.


Since I last updated this section of the blog, I also managed to file my tax returns for the first time as a full-time sole proprietor, which was…interesting to say the least. I’ve been doing my own taxes since I was a teenager. However, now that I’m a full-time freelancer there are many additional steps and processes I have to go through to make sure I’m doing the following: (1) claiming every applicable deduction; (2) filing the required forms since there are a few more I need to fill out that I’m used to; and (3) accounting for every bit of income correctly since I’m earning money through multiple channels these days.


With that said, I finally made a post with tips on how to approach doing your own taxes as a freelancer so that the process doesn’t turn into a nightmarish ordeal for you. Surviving tax season also underscored how important it is to either pay your taxes quarterly or be diligent about setting aside a certain amount from each paycheck to pay what you owe annually. Thankfully, I put aside a third of every payment I received from a client last year, and was able to pay what I owed Uncle Same pretty easily.


Now that my taxes have been paid, I’m currently working on paying off a small amount of credit card debt that I accumulated from traveling over the holidays. Once I’ve taken care of that I should be able to finally secure a designation agent for my company, and submit the LLC paperwork that’s been collecting dust on my desk.


What I’ve Learned

As I’m going through this process of building my own business that consists of well…me, I definitely find myself learning things that were never mentioned during my time at B school. These “teachable moments” have been both enlightening and frustrating experiences if I’m being honest. For one thing, it finally hit me that I’m trying my darndest to make something out of nothing and it’s honestly really freakin’ hard.


I have no previous experience as a business owner, no real contacts in the industry I’m working in, and no seed money to set-up my business. I fell into my position as a freelance writer, editor, and consultant after growing dissatisfied with my previous career trajectory and longing for something else. By trying out this freelance thing and learning how to build my business along the way, I’m pretty much building an airplane while simultaneously flying it.


That bit of knowledge brings me to my second insight, which is that growth isn’t linear. I’ve definitely taken 4 steps forward only to be forced to take 2 giant leaps back. However, even though this process has been pretty painful and has even caused me to question if I’m making the right choices at times, every step I’ve made have taught me a valuable lesson. I’ve been internalizing those lessons and using them to help me progress with much success.


I’ve also learned that being tired isn’t necessarily a bad thing. Being able to work diligently on projects of my choosing that I enjoy all day is truly a blessing, and there’s nothing like feeling exhausted after a long day of that kind of work. I also make it a point to consistently remind myself that just a little over a month ago I would have given anything to be as busy as I am now. This reminder forces me to recognize how volatile freelance life is and reminds me to savor moments when I’m being paid to be productive.


Speaking of savoring moments and working my butt off, freelance life has also taught me that saving your money is essential. If I hadn’t done a decent job saving the income I earned last year, I would have had to look into getting some kind of temp work to make ends meet and to pay my taxes and bills. Actually, the money I did manage to save was (and still is) more than enough for me to incorporate, but my January work drought underscored the importance of maintaining a Rainy Day Fund.


Where I’m Headed

I’m literally heading to Colorado this April for a housesitting gig I landed. (I booked the flight using credit card points for those of you wondering how I afforded it.) It will be my first time in Colorado and I’m super excited to spend some time in a new place. I also think it will give me a better work-life balance since I thrive in housesitting situations that force me to get out of the house and explore while also fulfilling various client obligations.


Professionally speaking I think I’m headed in the right direction. I’m at the point where I think I’ve planted enough seeds, and I look forward to nurturing the client relationships that I currently have, as well as the ones that are still forming. I really hope I can keep this plane airborne. Keep your fingers crossed for me.


5 thoughts on “Digital Nomad Tricks: Building a Plane While Also Flying It

  1. I love reading your stories about your freelance journey, very honest and relatable. Funny you’re going to Colorado. I’m here now for a mini spring break trip! The weather is crazy (it’s snowed twice since I’ve been here) but the mountains are beautiful. Hope you enjoy it!


  2. Thank you for the kind words. Also, what a coincidence it is that you’re currently in CO! I’m always looking for recommendations of things to do if you’d like to share.


  3. Well I honestly didn’t do a lot lol. Downtown Denver seemed to be the most interesting part though. There were a lot of arts centers and museums I would like to explore if I went there again. I went to a place called Taco Tequilas and Whiskey that had really good shrimp sliders. Hope that helps!

    Liked by 1 person

  4. I’m so happy you found me so that I could begin reading your posts. One thing I tried to break into 5 years ago was freelance writing and editing. I’m happy to meet someone who did it and is still doing it well. Happy to know you. 😘


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