Q1 Recap: 6 Unexpected Challenges Of Freelancing

I won’t lie.

There’s nothing better than waking up and deciding to stay home all day.

That’s the BEST thing about freelancing. No one has to tell me where to be, how to dress, what to do and if I don’t feel like talking to anyone all day, I don’t have to.

But that’s also the worst thing about freelancing. No structure.

Structure is one of the things I’m still figuring out, along with how to do taxes and a name for my business.

Think about it. If no one was making you get up and go to work Monday to Friday, would you be able to force yourself to? I bet if you had the choice, you’d probably skip a day or two, right?


I’m not saying that I expected freelancing would be easier than having a job. I knew it would be harder because I’m responsible for literally everything in my business.

Some of the challenges I faced during this quarter are welcome, and some I’d like to avoid in the future.

Let’s start with a positive challenge:

People hired me for many different types of projects.

This is what happens when you just keep saying “yes.”

Having a learner’s mindset allowed me to take on projects that were completely new to me without freaking out, like writing a sales page.

Here’s some of the stuff I worked on:

  • Writing educational blog posts for personal finance blogs
  • Ghostwriting blog posts for entrepreneurs and business owners
  • Writing LinkedIn profiles, bios, and Facebook “about” pages
  • Writing marketing copy and website copy for a new health food brand
  • Writing Craigslist ads
  • Copywriting for email drip campaigns, sales pages, and landing pages
  • Social media writing (writing out posts for Twitter, Facebook and LinkedIn)
  • Editing a manuscript
  • Writing under my own name for sites like Greatist and LeadWise

Yeah, someone actually paid me to write Craigslist ads.

Time management is a bitch.

I already touched on this a little bit, but time management is something I have to work on a lot harder next quarter.

The place I get really stuck? Figuring out when I can dedicate time to personal writing (like this blog) and client writing (that pays the bills).

It was so different when I had a 9-5 job. I could zone out for eight hours in the office, then come home and work on my side hustles until midnight without a problem.

Now? After a day of writing, all I want to do is cook healthy food, listen to podcasts, watch shitty TV and see friends.

It’s a work in progress. Here are some of the methods I’ve tried out to help beat procrastination and manage my time/tasks.

  • Trello: nope. Didn’t work for me. It’s very clunky.
  • Asana: LOVE this simple task manager, especially because it emails me my tasks every day.
  • The Pomodoro Technique: This worked for like, two weeks. Now? Not as much.
  • Trying to “theme” my weekdays. Meaning: Mondays I write, Tuesdays I do admin stuff, Wednesdays I take calls etc. That didn’t work at all. I have to write every day.
  • Blocking off time in my calendar for literally everything, including commuting. This works well some weeks and doesn’t some weeks, but I enjoy doing it. I like not thinking about what I have to do and when.

This is what my calendar looks like on a normal week:

Screenshot 2017-03-18 at 3.56.01 PM

Ideally, I’d be able to work from 7:00 am to 3:00 pm every day, then have the rest of the evening to work out, cook, produce content for my food blog and watch TV or whatever.

Freelancing is lonely.

I’m an extrovert, so working by myself has been hard on me and slightly depressing at times.

I’m not afraid or ashamed to say that life is pretty lonely right now. Of course, I have my amazing boyfriend, family and friends, but I don’t have anyone to regularly talk shop with.

I think one of my goals for the second quarter is to find that community feeling I crave so badly without forking over a lot of cash for it.

If anyone wants to talk shop about freelancing and actually be open about business numbers (um, money), reach out: taliasarakoren [at] gmail [dot] com.

I made my first hires.

Yeah, I’m a boss now. For real.

After encouragement from people I get to work closely with, like Julia Pimsleur of Million Dollar Women, I finally tried out the VA (virtual assistant) thing. I used UpWork to recruit my first hires because I’m most familiar with the platform.

I now have one steady “VA,” but she doesn’t schedule my meetings or anything like that. She’s actually a copywriter who acts as a second pair of eyes on everything I send to clients.

She’s a huge help and I’m actually enjoying working with someone, even though it’s a challenge. Luckily, I’m working with someone who understands that I’m learning how to manage people too.

I’ve also hired other people to do research for me, which is putting into practice the advice that I should delegate tasks that other people can totally take care of.

Hiring is a huge step in any freelance/entrepreneurial journey and I’m glad I finally took the plunge.

If you’re thinking about making your first hire, hit me up! I can share more about my experience with you.

I can’t work in the same place every day.

I had to stop working out of my apartment after about two weeks of freelancing.

Changing my scenery frequently helps me focus for some reason. In the last three months, I’ve tried a few places:

  • WeWork: Thanks to my generous mother, I’ve been using WeWork on her plan for free. Eventually, she’ll kick me off, though. I love the coffee here and I’ve met some nice people for sure.
  • Spacious: My friend Darrah Brustein told me about Spacious, a coworking space that uses restaurants during the day before they open for dinner. I really enjoyed working in these gorgeous restaurants in Manhattan. Since it’s a lot cheaper than WeWork, I’ll probably sign up at some point.
  • Ace hotel: I love going to the Ace hotel to work on weekends. Something about being there early, at like 8 am and leaving at 11:30 am when it gets crowded, makes me very productive. The only con? The coffee ain’t free.
  • Random coffee shops that have wifi: Okay, I don’t know when this happened, but I’m struggling to find good coffee shops in New York City that have wifi. Many of the ones I used to go to (that aren’t chains like Le Pain Quotidien or Coffee Bean) have just ditched wifi altogether.
  • My boyfriend’s apartment & my mom’s apartment: free wifi and good company, but with lots of distractions.

I struggle to dedicate time to stuff that’s important to me.

The time management struggle only gets worse.

My work/life balance is something I absolutely NEED to work on next quarter.

It’s gotten to the point where I make myself see friends twice a week (even though I’d rather be working, or am stressed about my workload).

While I used to run for an hour and work out for at least 40 minutes a few times a week, staying at the gym longer than 20 minutes is a challenge. I just start thinking about how much work I have to get done.

I also neglected Workweek Lunch, my food blog, for all of January and February because I had to focus on my business. However, in March I figured out a way to dive back in by scheduling an hour every morning to work on it.

View this post on Instagram

Sometimes my stretching routine involves selfies

A post shared by Talia Koren (@thetalillama) on


Like I said before, these challenges are welcome. I’m not scared of them. They’re not preventing me from getting the work done.

Challenges and failures are critical in the learning process.

For example, I learned that I have to strategically say yes and no instead of taking anything and everything that comes across my plate. I also learned that I’ll be WAY happier if I dedicate more time to the basics: sleep, exercise and being social.

A big reason why I was able to put my head down and work so hard this quarter is the 90-day-plan I created in January. Not only did it keep me motivated, it helped me make sure that every week, I was ONLY doing the work and tasks that would get me closer to my goal. You’ll be seeing a post about that next week!

How did this quarter go for you? I’d love to hear.

Reach out at taliasarakoren(at)gmail(dot)com. I read and respond to every email.


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