Business

Getting REAL: 17 of My Not-So-Pretty Imperfect Boss Moments

June 1, 2016
Imperfect Boss Moments

A few weeks ago I received an email from a blogger friend. I was SO excited by the content of the email, but had no idea how huge and inspiring it was going to become.

Ashley Beaudin from Fire & Wind Co. asked me, along with a group of amazing online entrepreneurs, to participate in a three day event called #TheImperfectBoss Campaign.

She said, “I want to ask you (with my big wild heart) if you would join me in this project in an effort to revolt against this pressure of perfection and rise as women owning our unique calling. Because perfection is a myth we must break through.”

Transparency and imperfection as a business owner are among my favorite topics.

As much as I love my career, it’s not easy and it’s nowhere near perfect. And you know what?
We’re ALL just figuring it out as we go. twitter icon

That was a resounding theme in the responses to the campaign on Instagram. Along with fear, rejection, and mistakes.

This week I’m joining a bunch of badass biz-owning babes in sharing what it really looks like to be a creative boss online. See them all 👉🏻 #theimperfectboss Mine is – my beautiful Badass Blog Planner got a bunch of reviews on Amazon that pretty much said “this thing sucks.” And even though it’s a tiny percentage of the number I’ve sold it still bums me out so much that I don’t allow myself to read them anymore. I’m still proud of it, it still sells really well. If some people don’t find it useful that’s a-ok. If I put any more thought into those negative reviews I’d never be able to put another blog post or course online again. And I love my job and my online peeps too much to let that happen. Feel free to join us by sharing your confessions with the hashtag #theimperfectboss 💛💛💛

A photo posted by Sarah Morgan (@xosarahmorgan) on

Another one of my favorites was the honesty about what a real day-in-the-life can look like for a digital entrepreneur.

Some people get the idea that “working from home” means staying cozy in your PJs and working from bed. Which is TRUE…kinda…sometimes.

The reality for most of us is more like what Kelsey describes below. Things get so hectic your priorities change from getting dressed and sitting at your organized desk in a pristine office to launching right into work no matter what you’re wearing or where you are.

And I can’t write this post without including this theme: overcoming the stigma and challenges of mental health.

I urge you to change your mindset. Instead of believing you will help others “once you have it all together,” instead realize that
you will help more people when they see that you struggle but are doing it anyway. twitter icon

Can we talk about how perfect is overrated? This time last year was tough. I was six months into being a business strategist, my generalized anxiety disorder intensified and then I found out why: I also have bipolar disorder II. PERFECT. 😬 I needed to let some time pass to process things, and to hang out with my therapist, but when @fireandwindco asked me to be part of #theimperfectboss I knew I had a good one! I know how lucky I am that my bipolar disorder is mild. I feel guilty that other people aren’t as lucky. I also don’t want to talk about it a bunch and be “the crazy business coach”… but I also don’t want to hide exactly who I am & where I’ve been. With a lot of work, tears & laughter, this year my business is booming & this is my husband’s first week working with me full time. So screw being perfect, bulletproof, airbrushed & obsessed with our brands. Let’s be ourselves, make a ruckus and be together while we can. Who’s with me? 😘

A photo posted by Kyla Roma (@kylaroma) on

While I planned to participate all three days, the reality was that I rushed to post something at 10pm the first day and then didn’t get around to doing any others. I did interact and learn a lot from everyone else, though.

Burn out is why I didn’t get around to the other days. Also, you’ll notice the bottom of this photo is cropped. I forgot “the” in the hashtag and couldn’t muster up the energy to retake the photo. hah!

Since there was such an amazing response, Ashley has made the campaign an ongoing thing. I’m pumped to be joining in when I can (and remember to) each Thursday.

For now, here are some of the real, imperfect boss moments that I hope help others realize that none of us live a polished-internet-ready life. I hope it inspires someone to realize that they can do it too, whatever “it” may be that they want.

17 of My Not-So-Pretty Imperfect Boss Moments:

  1. My big confession? I’ve had amazing results with clients when it comes to SEO, social media, blogging, etc. But my own content always falls to the back-burner. I have 200+ blog post drafts, my site doesn’t have the best SEO and I’m horrible at posting consistently on social media.
  2. It can take me 3 weeks to respond to emails.
  3. Client consultations on the phone still terrify me. If I schedule them late in the day it’s all I can focus on until it’s over.
  4. I would love for my Instagram account to be beautifully themed and color-coordinated, but at the same time, that restrictive rule gives me a bad feeling, and I haven’t been able to abide by it.
  5. I commit to too many projects.
  6. I’m afraid of Reddit because criticism is hard, and I’ll obsess over the troll comments, despite knowing I shouldn’t.
  7. Sometimes I don’t leave my house for days at a time.
  8. …..or get dressed. Or remember to eat until 3pm.
  9. I completed 75% of an ebook but never finished it.
  10. I struggle to “close sales” on the phone. I need time to process the call and decide on the best plan of action for the project.
  11. I’ve never written a full business plan for my own business.
  12. On multiple occasions I’ve opened documents that were supposed to be notes from a client consultation…and the document was blank.
  13. If I have a video meeting, you might see me in a nice shirt and make-up, but you can bet that 90% of the time I still have yoga pants on. I really hate pants. The best part is, most of my clients know this and laugh about it.
  14. I have a $500 camera “for my business” that I hardly know how to use
  15. I still don’t know what to call myself for a business title or what to use for a tagline.
  16. The comparison trap is an ongoing struggle.
  17. I hold back on my own marketing because I’m afraid of becoming overwhelmed with work or having to live up to a higher expectation.

But without these long roads, mistakes and experimentation, I wouldn’t have learned as much. I wouldn’t have seen what it actually takes to create and run all of the working parts of a business.

I wouldn’t be able to teach and help from a place of experience.

Join us! Learn more and sign up for the prompts here.

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  • Kayla June 1, 2016 at 7:50 am

    I love this SO much. I’m in the process of launching my own business and definitely think there’s this “glamorization” so to speak surrounding starting your own business, but it’s nice to hear the real side of things too and know that if I’m struggling I’m certainly not alone.

  • Kelsey June 1, 2016 at 7:51 am

    I can absolutely relate to so many of these! Thanks for sharing ☺️

  • Rebecca @ Strength and Sunshine June 1, 2016 at 9:44 am

    Haha, this is so good and so real!

  • Jaleccia June 1, 2016 at 11:36 am

    Man! All of this! I can relate! I love it!

  • Erin @ Erin's Inside Job June 1, 2016 at 2:00 pm

    Omg I love this. I saw these on IG and thought they were awesome. You know I love transparency too and this actually reminded me to get back to that some bc I feel like I haven’t been quite as raw lately in my posts. Great post!

    • lindsay Cotter June 2, 2016 at 6:29 am

      hey ya, i second erin. It’s good to step back and be raw/real. I needed this reminder! Thank you! <3 you

  • Jess @ Keeping It Real Food June 3, 2016 at 1:29 pm

    Thank you for sharing this! I struggle with a lot of these things too. Cheers to taking a step back and sharing the real story. I totally hear you about the comparison trap–and the unfinished manuscripts. I always seem to let stuff like laundry or cleaning eat up time I set aside for those things. It’s a learning process, I guess?