The Good, The Bad, The Ugly

An honest look at the perks and downsides of my creative business.

How many of you experienced the feeling of looking at another creative entrepreneur’s social media and thought “wow they’re business must be thriving.” Online it can appear as if creative entrepreneurs and freelancers drink latte’s all day and leave work early to go to the beach. What with all my pictures of palm trees I wouldn’t be surprised if someone thought that all I do is hang out at the beach all day long. Well today I’m going to give you a true behind the scenes look at the real perks and downsides of owning my own creative business. Feel free to comment below if your perks and downsides are similar to mine, I’d love to know I’m not alone!


  • I get to work with dreamy clients and do what I love.
  • On occasion I get paid for drawing whatever I want.
  • I determine my own schedule.
  • My office, my rules.
  • I decide which projects to take on and who I want to work with.
  • I take breaks at the beach whenever I want.
  • Owning my own creative studio makes me seem more interesting and is a great conversation starter.
  • I can take time off whenever I want.
  • I get to be involved in all aspects of my business.
  • At previous jobs I was seen as only the graphic designer but with Little Trailer Studio my clients trust my business advice and really respect my expertise.
  • I help other creative entrepreneurs create their dream businesses.
  • I get to collaborate with other creatives.
  • I learn something new everyday (or at least every other day).
  • I’m testing my strengths (and weaknesses) more than I have at any of my previous jobs.
  • My coffee dates (among other things) are all tax write-offs.
  • Seeing my clients’ face light up when I show them their new brand identity/website really makes my day.
  • My errands include going to the art store, networking with other #girlbosses, going to museum exhibits.
  • I’m creating something that is truly mine — my successes are my own and my failures are my own.
  • This is my favorite job position I’ve ever had.


  • Sometimes those dreamy clients aren’t always that dreamy.
  • The amount of projects I get are inconsistent.
  • I don’t always charge what I know I’m worth.
  • Since I’m a one-person-show I have to play art director, graphic designer, web developer, SEO master, among others so feeling like I have to know how to do everything can be exhausting.
  • There is no one but me to hold myself accountable.
  • I have to do things I don’t enjoy like cold emailing and negotiating contracts.
  • The whole idea of “I can work wherever I want” hasn’t proven to be successful for me yet.
  • I get to determine my own schedule but I usually stick to a regular 9–5 schedule.
  • I am not a marketing guru.
  • It can be difficult not to obsess over numbers and metrics.
  • My errands include being on the phone with the internet company, my bank, and other folks I don’t really care to talk to.
  • I really miss having an IT person to fix my tech problems.
  • Worrying about doing my taxes for fear that I’ll owe money (money I don’t have).
  • Success is a twistier-turnier journey than I thought it’d be.


  • Checking my mailbox daily for the last two weeks, waiting for a $2k check from a project I worked on months ago.
  • My gorgeous Instagram photos don’t always translate to clients and paychecks.
  • My salary is lower than what it was at my last job.
  • Accepting failed projects and learning from them.