On Working For Myself

Tuesday, October 18, 2016

In the midst of decluttering our house I came across a phone book sized book of coupons. Like actual coupons you hold in your hand, not the type on your phone.

Did you know these books still exists? And businesses pay money to be in them.

I know because two years ago, in the summer of 2014 I attempted to be a coupon sales woman. I physically cold-called on any business that would let me inside and would say, "Hi, can I talk to your manager about coupons?"

I found the job on Craigslist (red flag #1.)

I emailed the manager and was hired without an interview (red flag #2.)

And then I set up a meeting with the manager at a coffee shop that was supposed to happen two days later. He didn't show, but emailed me all the pdfs, and then sent me the coupon book in the mail. (red flag #9000.)

I feel like I need to say that at this time in my life I had held several "real professional" jobs prior to this coupon blip. It wasn't as if I was fresh out of college or anything. I was simply at that point where my blog was starting to make money, but it wasn't completely there, so I needed something to help me get by and I refused to work a standard 9-5.

And so I thought a "work at your own pace" coupon sales job was the answer. It wasn't.

But never the less, I would put on my "work attire" and walk door to door, downtown Chicago, peddling my coupon books.

"Hi, I'm Taylor. Can we talk about coupons for a bit?"

Again, this wasn't ages ago. This was in July of 2014. I did it because I had to pay rent. And the idea of going back to a cubicle and working a job that ate my soul was not going to happen. I wouldn't let it. Every single morning I would get up and write in my goal notebook, "I WILL NEVER WORK FOR ANYONE BUT ME. EVER AGAIN.

I still write this today (every single day) just to be certain. Because when you work for yourself the feeling of someone sweeping the rug out from under you is always there.

I did this job for about three weeks (it was straight commission, no salary at all) and I was terrible at it. So one day I decided to take a chance and order 25 t-shirts with a phrase I thought might sell, "TALK HERBIE TO ME." I put the first order on my credit card because I didn't have enough in my bank account to cover. And I went back and forth about it for nearly a week before finally doing it.

I took my first 25 orders via email. They sold out in about an hour and I was just so thrilled I could pay my bill. I remember telling Chris, I bet I could sell 200 by Christmas. It seemed so crazy.

I'm about to hit 10,000+ orders for 2016. I feel boastful writing this, and perhaps I am, but really I'm just grateful.

So I'm not throwing out the coupon book.

I'm going to keep it because it reminds me to hustle. And then hustle more. I have about two hours of packing shirts to do tonight. I need to count inventory, come up with new marketing ideas, new designs, ext ext. And before I found that coupon book I was feeling just a little bit pissy about it all because I know I'll be up well past midnight.

But even when I'm pissy, I am still grateful. I'm grateful I put that first order of 25 shirts on my credit card in late July of 2014.

However, I don't want this post to come off as preachy or "if I can do it anyone can" because I know that's not true. It's easy(er) to take risks on a new business when you have a safety net under you. (Parents who will bail you out.) I knew that if I really found myself in a bind my parents would help out, as they always have. And so many people don't have this luxury.

But the post about "giving myself a privilege check" whenever I feel too high and mighty will have to come at another time.

Because for now, this post is just about me feeling grateful I get to do what I do. And mostly that I get to spend my mornings on the couch with Harlow in my lap as I answer customer emails. I wouldn't trade my mornings with Harlow for anything.

But enough chit chat, it's time to get back to the hustle.

To each and every one of you, thank you for supporting my business. I really really appreciate it.


  1. Love this. I am finding myself questioning if I can "take the leap" and go full time with my photography (I know, isn't everyone?!!). I literally don't sleep between my "real" job and my photography business, but making that change scares the ever living shit out of me. I would LOVE to read a post about how you make it all work!! My fiance would appreciate me to cite my sources when I tell him it's okay if I quit and become a stay at home dog mom.

  2. You are amazing! I am so inspired by how hard you work and the fact that you've turned all this into a business! Congratulations on all you've accomplished

  3. It's amazing how far your business has come! That must have been such a cool feeling to sell out of your first round of shirts so quickly.

  4. Definitely one of the things I admire about you most is your work ethic. I feel lucky to call you a friend and get to chat with you about the craziness of the path we chose, but wouldn't change it for the world.

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  6. You're such an inspiration, Taylor! A true bad ass and I've enjoyed watching your business grow. Brag a little bit sister, you deserve it!

    Fallon // Mountains & Mimosas

  7. You're definitely a role model to all the wannabe stay at home dog moms out there! Harlow and the blogging world are lucky to have you!

  8. You are kicking so much ass. Keep it up! We love you!
    XO Ellen from Ask Away

  9. 10,000! That's amazing! You've sent 10,000 of your babies out and about into the world hehe :) congrats girl! #girlswhohustle rock!

  10. My goal is to one day work for myself (and the sooner the best because the office life blows haha). Props to you girl - keep doing it!

    xo, Maddy

  11. Congrats on 10k! Random question - do you have a 5 year plan? Or being an entrepreneur is it a "whatever comes my way"?

  12. 10,000!! That's freaking phenomenal and you forgot to mention that you are so good at it that errrrrbody tryin' to copy you. I love that you do it in part for the puppies.

  13. Congratulations to you on all of your success! This gives me lots of hope because I'm in the beginning stages of starting my own business and the doubt has crept up on me and made me afraid to move forward. You've done really well! I also have a really great safety net, which gave me the original confidence to go for this, but it's still really scary to make those first big steps.

  14. Any chance you need to hire a virtual assistant? ;) No, but seriously...

  15. This is definitely inspiring to read about. I know I've had some really mundane stupid jobs (also found on Craigslist) so I can relate to the struggle! (:

  16. So relevant for me to read this. I'm making the plans to transition from the "9-5" and work for myself full time and its terrifying. It involves a lot of hustling right now, trying to do it "all" so soon, I can do just the things I want to do (and do them with my pup on my lap because, duh - dream). Thanks for posting!

  17. When will the COZY AF sweatshirts be restocked! They sold out so quick!!

  18. Congratulations on hitting 10,000 orders! Whenever I wear your Married AF shirt, I get compliments and have referred many of my about to be married girlfriends to your site. Keep on hustlin' Taylor!

  19. Wondering if anyone has ever told you the abbreviation for etcetera is etc and not ext? You may have a completely valid reason for using ext. Maybe someone already told you and you vowed to forever use ext just to annoy them. In which case, you would be my spirit animal. LOL! Anyway, I just thought I would put it out there. P.S. Harlow rocks!

  20. Those big books of coupons are sold here through schools and day cares for them to raise money but I don't know anyone who has bought them or used the coupons in them, just saying.
    Tee shirts well who doesn't love a good tee shirt with something written on it

  21. I love this so much! I think you need to frame that coupon book. What a great reminder :) And congrats on hitting 10k, that's so amazing!

  22. dude...it's AWESOME to see you acknowledge the privilege that you had while chasing your dreams. SO OFTEN I see people (my peers etc) say "if you want to move, just do it?" or "if you want to go to school for that, go for it!" or "quit your job, just do it!" and these same people are the ones who have their safety net of parents, helping them when times get tough. I'm happy for them, but I absolutely cannot relate as someone who doesn't really have a safety net (other than moving back into my childhood room...but I'm grateful for even that!). Anyway I'm glad your business has come so far but I just wanted to comment on how refreshing it is to see someone not bullshit and peddle the "anyone can do it!" story when it's often not that simple.

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