Caylee Grey
Fairy art mother


Ten things I have learned after one month of self-employment

The Pantsless Entrepreneur | Things I Have Learned After One Month of Self-Employment ‚ô• Caylee Grey

Today marks my official one month anniversary of being self-employed. Boy, oh boy, it’s been a ride. A good ride. A rollercoaster ride that only goes up (thanks, Augustus Waters¬†[and V]).

My ten favourite lessons after one month of self employment

1. It’s amazing

Obviously. I always knew that it would be. But actually being in the thick of it? Yep, pretty amazing.

2. People are incredibly supportive

I can’t even handle the amount of support I’ve been given. It feels as though I’ve had a baby. I received emails, and comments, and direct messages, Whatsapps, and phone calls, and Skypes, and videos, and voice recordings, and photos, and snail mail. I saved every single one of them to a folder on my computer. I was blown away every time my phone beeped. I had to charge my cellphone five times to keep up. Internet people are easy, because mainly they get you, but real life people? To me, they were the struggle when I made the grand declaration. That’s why I needed to make a Facebook page. Make it legit. Make it real – not only to internet friends. But that’s a story for another day. At the end of the day I received a long letter from a friend in high school. It got me bawling. Happy bawling.

There is just so much love, and support in this world, especially from the people you don’t expect. You’ve just got to¬†keep opening yourself up and one day it will be worth it.

3. My customers are the best

Seriously.¬†There’s just something special about customers in the creative realm. Corporate customers suck, and these are the only ones I’ve ever known until now. Every person who purchases a planner from my shop, every person whose blog I design, even the corporate¬†branding customers…they all feel like old friends. They’re on the same wavelength, and all I want to do is see them happy.

Support from a customer (in the non-monetary sense) is a beautiful, beautiful thing, and I treasure every single person who chooses to spend both their time, and their money on what I have made. I will always try my supreme best to make it worth it for them, whether it is a $5 order, or a $500 order.

4. My best working hours are okay

I put a lot of pressure on myself to work¬†an entire day in the beginning. By entire day, I mean 9¬†to 5. Husband would get home, we’d eat, and then I’d be so excited that I’d be back at my computer until late. After copious amounts of chats with Andrea (Queen of Routine and Being on Top of Things), I realised that if I didn’t change something while I still had all this enthusiasm, I’d burn out.

I realised that I work like an absolute beast between when I wake up and lunchtime, and then in the evenings.¬†Between lunch and dinner I’m positively useless and can probably just send a few emails. And so. Because I’m my own boss and I do what I want, I changed my working hours. They are now 8 to noon, and after dinner to 10. That’s still eight hours and a full working day. Since T has been in England on business, I’ve been naughty and had working hours until 4am. Work really is play for me. I’ve been doing the Pomodoro technique for getting work done, and during my breaks I just tend to do a different/easier work-related task.

5. Structure is necessary

This is a biggie. Now that this is my income, I need to make sure that I’m reaching my goals and the¬†first step to doing this is actually having these goals. Every morning I write out my MITs for the day, and then I go ahead and do them. Instead of just doing what I feel like, I have a rough plan and I’m¬†doing that. It feels good.

My days look like this: 06.30/07.00 natural wake up. Fancy coffee and water. Upstairs. Write MITs. Do one MIT. Make breakfast and eat while listening to The Bible (The Message) audiobook.¬†Read actual physical Bible and write any notes down. Make new coffee. Go upstairs and it’s MIT #2 time.¬†Work until lunch time. Eat. Watch series or Lynda video. Park with Griffin. Errands. Be lazy.¬†Start dinner. T comes home. Eat dinner. Back upstairs for MIT #3 and all that. T comes upstairs to play games on his computer so it works out well. Work. Create. Email is¬†not checked and responded to obsessively. I’m on email rehab. Bed whenever I’m tired. Great day.

6. The best business partners and the best meetings

I’ve made my husband my Chief Financial Officer and Griffin my assistant. If I want to make a business expense, I first ask¬†T. He would never presume to control my money, but he’s such a great sounding board. He’s really great with our money, so he’s really great with my business money. He has no qualms telling me that spending $100 on sparkly gold paper is not really a business expense. Griffin is the best assistant because he ensures that I don’t get too in my head and on my computer¬†by making sure that I feed and love him. Puppy cuddles are the best way to spend a break.

I’ve also started moving¬†some work tasks to places other than my desk. Hello, inspiration! Parks during lunch hour, coffee shop Moleskine writing, setting MITs and goals during a breakfast. I can’t remember who said it, but they mentioned having business meetings with yourself. This has been a game changer.

7. It’s not about the money but the money certainly helps

Unfortunately, money is a pretty solid indicator of how successful something is going. So, while I never went on my own for the money (and will hopefully never again work for money), there’s just such a satisfaction knowing that people are willing to give¬†their¬†hard earned money for something you’ve made yourself.

I’m beyond proud of myself that in my first month of my own business, I made more money than I’ve ever made in any other job¬†including corporate. This is big for me. Again, my focus is not on money, but my parents would not completely understand if I told them that I made the best wedding planner I’ve ever made, or pleased my most favourite client ever. They 100% understand numbers.

You know?

8. Customer service is #1

Obvs. Customers are my focus. If someone took the time to write to me, or ask a question, then I’m going to take the time, as soon as humanly possible, to respond to them fully.¬†I’ve even written out my business rules when speaking to a customer so that I have a (high) standard.

9. I’m better and customers are happier when I’m human

In the beginning I tried to be formal and business-like. Nope. Customers are humans too, and¬†in the business I am in, they like to work with humans too. I’m happier when I can be myself and informal, and say silly things, and they’re usually happier too because then they’re allowed to be themselves too. And boy, how I love them.

10. Pants by choice is the greatest

I don’t necessarily have to not be wearing pants to be happy, but I really like not being forced to.

The Pantsless Entrepreneur | Things I Have Learned After One Month of Self-Employment ‚ô• Caylee Grey

If you haven’t yet, you can like my Facebook page and keep up to date with what I’ve been up to. Mostly.¬†Facebook has never been my favourite¬†social media but I’m getting there.

A special thanks to my cousin for my superhero name / future book title.


  • Ines T

    Loved this post Caylee, SO HAPPY you’re doing so amazingly well!! And I’m seriously impressed it only took you one month to figure out your routine, it took me like a year!

    7 Aug 2014
  • A month already? Glad it’s all going amazing for you but I knew it would:) And yes, fur baby cuddles are definitely the very very best!

    7 Aug 2014
  • YAY!! Congrats on one year of not having to wear pants! I am so jealous! Your creativeness is such a shining spot in this world.

    7 Aug 2014
  • Aaaaahhh.
    I don’t even know what to say, Caylee. I’m so SO VERY happy, proud and inspired by you.
    You’re on fire and I love your enthusiasm and dedication. Don’t ever lose your sparkle.


    7 Aug 2014
  • best ever! love this!!

    8 Aug 2014
  • Roos

    I’m not surprised this is working out so well for you. Besides the fact that you create beautiful things (in my opinion), you come across as real which is why people can relate to you.

    8 Aug 2014
  • You are SO inspiring. I love that you’ve already come up with such great lessons after only a month. Keep going, I’m taking notes ;)

    8 Aug 2014
  • Robynn

    What Ines said. You are ROCKING this thing, and so soon! Amazing.

    Also, I 100% second #3. The best part of running Purlescence was dealing with amazing customers and equally amazing suppliers. In the hand knitting industry, basically everyone is living their passion; they’re incredibly excited about what they do, your customers are equally excited, there’s just so much energy and enthusiasm coming from all sides, it makes for the *best* business interactions imaginable.

    Also, yer welcome. ;-)

    8 Aug 2014
  • This is amazing, Caylee! I’m so happy for you – your enthusiasm and passion for your work are so infectious that I’m smiling from ear to ear! You are such an inspiration and are proving again and again that this is a brilliant career choice. Well done you, and I can’t wait to read more about your entrepreneur adventures!

    10 Aug 2014
  • Hello Caylee! Only just catching up on your posts now, and hadn’t even realised you’d made the leap to full-time freelancing. Congratulations! Looking forward to coming along for the ride. :)
    Ronnie xo

    11 Aug 2014
  • I finally found time to read through this. So much insight. I’m so so happy for the journey you’re going and so proud of you. And when you are the biggest thing I can say, I was there in the beginning. (wohoo!!) :) This makes me all happy.

    15 Aug 2014
  • What a wonderful re-cap. You’re learning so much already! I can’t wait to see what happens next.

    20 Aug 2014
  • Ahh this is so inspiring, it makes me wanna *dive* into the ocean of self-employment! I’m so happy you’ve got so much support and love surrounding you.

    22 Aug 2014

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