Chanele’s Check-In: January 2018

In January, I…

But I was disappointed that…

  • I wish I read more (I know, a weird thing to be disappointed about but even though I’m much busier, I really want to do a better job at setting aside time to read each day as it relaxes me!)

In February, I’m looking forward to…

  • The 2 year anniversary of Do Well Dress Well on February 1st! (although at the time of publishing this post, it has already passed!)
  • Hosting an in-person workshop on pitching in partnership with Workshops by Huda
  • The launch of the blog for Make Lemonade (Yours truly is the Editor-in-Chief!)

Books I Read

The Seven Husbands of Evelyn Hugo by Taylor Jenkins Reid

(I tried to read A Man Called Ove but found it too morbid and I couldn’t even make it through 2 chapters of The Subtle Art of Giving a F*ck)

“So, how are you? How are you liking working for yourself?”

If I had a dollar for everytime someone has asked me this in the last few weeks, I’d be a millionaire! But, how am I? I’m exhausted but I’ve never felt more fulfilled in my entire life. Since resigning from my job last November, life has been a complete whirlwind. From meetings to proposals to keeping up with content on the site to rebranding, my to-do list is pretty much a never-ending list at this point in time. However, although I’m keeping myself busy, I’ll admit that I’m scared every single day. Don’t get me wrong – I don’t regret my decision one bit but reality really hit me in the face when I first experienced not getting my usual bi-weekly direct deposit from work. I may or may not have cried. Wow, this is real now.

I am learning everyday to allow the space between where I am and where I want to be to inspire me and not terrify me. – Tracee Ellis Ross

The biggest adjustment for me has been the change in my spending. I’ve mentioned in other check-in posts that I used to find a lot of comfort in buying clothes regularly and I used to buy my lunch every single day when I was working full-time. I had to get rid of those habits very quickly now that I’m on a “new entrepreneur budget.” I will maybe buy 1 or 2 new items if I have an important event or speaking engagement but that depends if I have room in my budget. I no longer shop for no reason. Another thing I had to change? My book habit. I love buying new books. I love the feeling of the pages in my hands but I never realized how much buying physical books can add up! I vowed that I’d never read e-Books but in February, I’m going to start!

I’m not making millions (yet!) and I never want to become a burden on my husband and family. Yet, there are some days that the thought of that really consumes me. To the point where I’ll spend 30 minutes scrolling through new job postings as I’ve somehow convinced myself that I made the wrong decision. Then, I snap back to reality. I am doing this. I can do this and I will be successful. The problem is – I’ve never been someone that likes to ask for help. It’s a weakness, I know. But if there’s one thing I’ve learned throughout this journey – I have to acknowledge when I need help and then speak up. Whether that’s help with a particular business task or help with finances, I’ve had to get over myself very quickly. I just can’t wait for the day that I can return all of the favours that have so generously been provided to me.

In the meantime, I also applied for a business pitch competition! I never realized how much money is available to new entrepreneurs and I’ve enjoyed the experience of putting together my pitch deck. I find out towards the end of February if I’ve made it to the finals and then I’ll have to pitch live in front of judges. Even though there’s always the chance I won’t get it, I plan to watch a lot more Shark Tank and Dragon’s Den as a way to brush up on my pitching skills. Cross your fingers for me!

Aside from the financial side of things, I’ve also found that I’ve had to really stay on top of my mental health. In the first few weeks of December, I had a lot of trouble sleeping. I would stay up till 3-4am and I’d just be staring aimlessly at the ceiling thinking about the magnitude of the decision I just made. Don’t forget – I am not a risk taker. This is the biggest life change I’ve ever made and it took me a long time to come to terms with my “new normal.” I also found that I’ve become a lot more emotional and I can get really caught up in my own thoughts. I find so much enjoyment in working from Make Lemonade, a co-working space for women in Toronto. Being able to get out of the house 1 or 2 days a week and work alongside so many like-minded women has been invaluable for me. Thankfully, my sleeping patterns are back to normal but self-care and surrounding myself with other people has become more important than ever for me.

When I first left my job, I thought that people would think I’m just caught up in the “Girlboss” hype. I mean, after all, it was only a few weeks prior to my resignation that I attended the Girlboss Rally in NYC.

Let me tell you right now – although I love being a “girlboss” by title, I am very much aware of the reality of it…and I still love it. There’s some weeks where I don’t leave my house for 5 whole days and I’m just powering through my to-do list. I love that. There’s some weeks where I can’t afford to spend any money at all. There’s also some weeks where I get so many rejections, my clients are late paying me and everything seems like it’s going wrong. I still love it. I may cry and I may get extremely frustrated. But, I still love it. Even when my entire face begins to break out with stress pimples. (Yes, that has happened!)

If you’re looking for me to tell you that this whole “girlboss” thing is a piece of cake, you’re in the wrong place. Being a full-time entrepreneur is one of the hardest yet most fulfilling thing I’ve ever done. You have to make sacrifices you’ve never made before and it is not as glamorous as it seems on social media. My goal is to share both the good, bad and ugly of this experience because we need to see a little more authenticity!

The Evolution of Do Well Dress Well

2018 marks what I’ve been caling Do Well Dress Well 2.0. It has changed so much since I first launched in 2016 and for the last few months, I haven’t felt like the current branding has reflected it’s growth. It has grown from being just a “personal blog” but I realized I didn’t really do my part in communicating that effectively. Since November, I’ve been brainstorming and trying to come up with a new brand aesthetic that best fits what Do Well Dress Well has evolved to and what it will become in the future. I wanted something bolder, brighter yet a little more simplistic. I wanted it to reflect the type of woman that reads the site and finds value from this content. Yes, this will now be the third (and final!) logo change but through this journey, I’ve decided to just ideate, create then iterate.

Here’s a little flashback of the various logos of Do Well Dress Well:

This was the first logo that was used at launch in February 2016. It makes me cringe when I look at it now but thank goodness for growth! I’ll admit, I rushed this one by creating it in Canva because I just wanted to make the site live. I was tired of always holding myself back and convincing myself that I wasn’t ready. I also did not envision Do Well Dress Well as a business at this point.

This was the second logo that I commissioned as a custom piece by the lovely Joanna Pop. I loved how the shoe and cellphone represented both elements of the Do Well Dress Well brand.

And now, the third and final logo for Do Well Dress Well displayed in multiple colours:

It was really important that I eliminated the colour black from the logo. Do Well Dress Well has come to be associated with all things colour and so the logo no longer reflected that. I also wanted something more timeless and would represent the type of woman this platform is for – women in transformation.

Like butterflies, I’ve come to realize that the women that enjoy reading Do Well Dress Well are in transformation. Whether it’s from school to full-time work, switching jobs or industries or trying to take their side hustle full-time, one thing is for sure – they’re always trying to become a better version of themselves. They don’t have things all figured out and that’s completely okay because they’re determined to keep learning, evolving and seeing the world in colour.

As Do Well Dress Well prepares to transform into a social enterprise, I wanted the imagery to represent this as well. My goal with this platform is that it empowers women so they empower other women. Through the scholarship that will launch this year and other opportunities to “pay it forward”, I’m excited to see us collectively evolve into the women we want to be. 

So, there ya go! If you’ve been wondering what I’ve been up to – now you know! Can’t wait to reveal more over the coming weeks.

Want to stay up to date with all of the upcoming changes? Be sure to sign up for the Do Well Dress Well list! When the new site design goes live later this month, you can expect to receive regular emails with valuable content, upcoming events and more!

Until next month,



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1 Comment

  • Reply
    Jessica K
    February 6, 2018 at 10:16 pm

    I love this update!! And the new logo and new looks.. I am so excited for you Chanele! I feel like somehow I’m following your footsteps.. I cannot wait to see what 2018 has in store for you. Go DWDW!

    Jessica || Cubicle Chic

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