Like you, I’m an Imperfect Boss, too

Confession time:  She is an Imperfect Boss. This Fall was a winding road, and I have so many confessions on my heart. I hope you’ll hear me, loves.

imperfect boss

My last blog release was almost a month ago, a lot has changed, and my heart feels heavy that my blog has been untouched. Imperfect Boss Rising. My mind is running the tape reels of headline movies such as:  ‘This Isn’t How You Do Business’, ‘What Business Plan?‘, and the nail-biting ‘ A Failure’s Guide to Entrepreneurship’.

When things don’t go to plan

The seasons are changing and something is stirring. It’s been 6 months since I’ve worked a conventional 9-5. It has been the most turbulent, change-soaked, tragically-terrific time of my life. I am not yet 100% self-sustainable business but I am palpably close. Not there yet; ever becoming.

If you’ve been following me for a while you might be aware of my ANTI-Busy Revolution, but here’s confession one:  I’m busy, too. UGH! My mini-revolution is just as much about me as it is others! If I’m not run off my feet and sleep deprived, I tend to undervalue the work I’m doing. ‘If it doesn’t cause me to falter, is it worth it?’ Trust me, I am just like you.

There’s an-almost-impenetrable-cycle to break here. The struggle has taken a variety of forms, but I started to notice I needed something more. My time intensity wanes from ‘overrun’ to ‘under-taxed’ in my coaching business, and I recently felt the tug for a gear-shift. The guilt shadows illuminated and hid a new need for something more than just KD and You. And then there was unexpected knock on the door.

When opportunity knocks

I was approached by someone I implicitly trust and respect about an opportunity in Toronto. I can’t lie – I experienced ALL the feels. Too many feels. I sat on them feels for months, and on the third door-knock I began to question what the universe was offering me.

I’m an analyst and strategist at heart, and this new opportunity didn’t seem to fit my current plan — until I opened my eyes to the possibility of what it could be and what it could give me. The excitement of feeling valued + being invaluable, the adventure of travelling for work, and the opportunity to network across the country started. Confession two: I was tempted by a 9-5 job.

At the same time, buried beneath the sweet taste of temptation lay the bitter sting of guilt. Guilt for even considering leaving my baby — my KD and You Coaching business. She’s so small + young, and I have spent every day of the last 11 months of her infancy breathing life into her. I’ve stayed awake countless nights, agonized over her nutrition and given her every second of my attention. Was KD and You ready to share my attention with a long-lost brother or sister?

With my stomach in knots, I wondered how I would duplicate myself to have it all: adventure, travel, flexibility of time, coaching freedom, 9-5 stability, etc. My guilt gremlins told me I needed to choose, and I was buying it. ‘You can’t have a successful business and a work a 9-5′, ‘this goes against your no 9-5 defiance identity‘, ‘forget solopreneur, you’re sell-out-preneur’.

I am the imperfect boss

the imperfect boss

I am laser-focused towards my dreams, but thankfully I have more than one dream at any time. Yes, I want to run a successful coaching practice full-time BUT I also desire adventure, freedom + spontaneity. While my coaching practice is the most fulfilling aspect of my life, I still crave to live in and from the depths of my values more. And even as an entrepreneur with an abundance of time and flexibility, I wasn’t!

The 9-5 decision deadline loomed and my head spun with a thousand thoughts, but it all came done to one thing:  What would it be like to have it all? Ha! I hadn’t even entertained the idea that I could do both. I was so protective of my baby that I shut myself off from other opportunities. I was living in a scarcity mindset – ‘what if I do this and I can’t go back to the way things were?I was living in a black and white world – ‘what if I have to give up my business while I work a 9-5’? I was replaying my old movie of fraudulence – ‘who am I if I give up the entrepreneurial struggle?

For anyone running a business while working a 9-5, I want you to hear me loud and clear:

Your circumstances don’t define you

Elizabeth Gilbert spoke talks about the insanity we succumb to when we force our creative endeavours to become our bread and butter. We force ourselves to perform. What are we when we are under pressure? Inauthentic, less than our best, and far removed from ourselves.

The worst part of the struggle I experienced was the titles that were being imposed. Side hustle vs. Full Time Job. If I work a 9-5 is that must be my priority, right? WRONG! So many creative entrepreneurs use time-spent as a quantitative measure of heart-felt investment. Don’t fall into that trap. What sets your soul on fire is your identity, not the time amount of time you sit behind your desk.



Entrepreneurship is messy. I’ve felt the turbulence of identity-crisis, especially when it comes to owning a business and working a full-time job. What has helped me maintain my business-focus and career-identity has been something coaches call reframing.

When a coach reframes a situation, they take the original information and interprets it in a different way. The fog of guilt dissipated when I realized that my love for KD and You and clients isn’t intrinsically linked to the amount of time I spend with them. The positive correlation of who I am is defined by… what I am! Imagine that. My full-time work has no bearing on the identity I hold as a Success Coach, because I do not ‘do’ success coaching. I am a Success Coach.

Similarly, my end goal is to BE a Success Coach full-time. It’s where my heart lies, it’s the fiery passion that runs through my veins — my lifeblood. The full-time work has a dual function: it fulfills my heart-centered values and provides a safe support structure for my coaching practice. There is no need to assign titles such as ‘side-hustle’ and ‘real job’.

While the client-scheduling and working across miles and time zones is logistically insane, my business hasn’t suffered because of full-time work I’ve engaged. KD and You and my 9-5 are symbiotically linked to fulfill me in different ways. For example, it’s a Saturday morning and I’m in Toronto working for the morning before I go play in this bustling city. So my question to you is:

How can you REFRAME Your 9-5 as a support structure for your creative passion?

imperfect boss

Well, I guess the cat’s out of the bag. I have accepted the Toronto offer, and will do it for so long as my entrepreneurial spirit remains in tact. I am an Imperfect Boss –  I run a business and work full-time. So what?


Reframing is my favourite coaching tool, and yes, I use my skills on myself when I recognize my stuck-ness! I reframed my situation to embrace myself as an Imperfect Boss who is open to all opportunities. I make mistakes, I make changes, and I make it all work for me. Only I can define myself and at the end of the day, I only have myself to answer to for how I feel.

Moral of the story

You get to choose. You get to choose to run a situation or have it run you. What I’m really saying is embrace your inner Imperfect Boss, and the messiness that is entrepreneurship. Don’t fall into the trap of a rigid identity. Define yourself FOR yourself.

I’ve alluded to it before: the all-or-nothing mindset secludes you to one-or-the-other outcomes and dismisses the nuanced grey area! You are an ever-evolving and seasonal being. Experiences and decisions will paint your canvas, change your mind and shift your being. You are the Author[ity] of your Life, and only you get to choose how you present yourself.

I don’t what’s going on in your entrepreneurial world, but I guarantee you will find peace in the middle of your guilt storm when your creative-based businesses and your financial security job can co-exist in collaborative respect. Guiltlessly embrace your Imperfect Boss.

With love,



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