The Shoes that Sparked My Confidence: Stepping into Myself & Success

women in business, women entrepreneurship, honesty

The walk towards freedom from myself started with a pair of shoes.

No,  it started when I was asked to be one of the leaders of Spark Retreat this May.

No, it was the day I realized I was scared of my own power and was holding myself back from the life I want…

Whatever catalyzed my decision to make peace with my self-doubt, the shoes were a symbol of stepping into my power, and getting comfortable with my own face again.

The back story…

Since we are talking about ethics and big, meaningful words like authenticity and integrity, I need to be honest about one of my own deepest struggles. I am just as shy, self-conscious and afraid as any one! Seeing my face on the internet freaks me right out. I have difficulty caring for myself or seeing my own value with the same compassion I lavish on others. I take on too much and then feel overwhelmed by my inability to be super woman. I have big ideas so push myself constantly towards an indefinable goal, without taking the time to see how far I have come, or where I am right now.

I project a strength and confidence that leads people to think I am tougher then I really am. An illusion helped by my big hair, big smile and big laugh-even when my heart is pounding like a crazed bird in my chest. My love of community forces me out of my fear because that love of connection is stronger then my shyness. This projected confidence has also gotten me in a lot of trouble. I can’t tell you how many times I’ve been told to laugh quieter, speak with less conviction, and keep my thoughts to myself. Supervisors told me I was intimidating. Boyfriends told me I was too strong. After I had kids I felt out of place with the more timid parents and stuck out like a sore thumb at playgroups.

So I started to play smaller and shrink myself into something more manageable. It wasn’t even a conscious decision! I love bright clothes, fun hair, big earrings and funky shoes but I bought neutrals so I didn’t stand out so much. I stopped being me in all my muchness. As I shrunk into this smaller, tamer me, I put my energy and passion into OMHG and our community. I started out by playing small and trying not to put off any of our original readers.  Over time I realized the more I showed my ‘true’ self, that loud, bright, curious, sensitive girl I am inside, the stronger our community became and the more I called my biggest supporters to me. The more people saw me even without having my face all over the site.

jessika hepburn

While I don’t ever want OMHG to be all about me or become a ‘personal brand’ what I want is for all of us to feel empowered and safe to be ourselves here. I want us to see our own beauty and value, our diversity, and uniqueness. I want that for myself too. If I want that to happen I need to stop being so afraid of seeing the success I have created here. I need to give myself the same love I have endless amounts of for others. I needed a headshot that wasn’t taken by my small child and a real about page.

I find it much easier to give the credit away then to own any of it. Owning it means I accept responsibility for shining my brightest when it is less scary to sit back and encourage YOU to shine. Why is it so much harder to see our own radiance then it is to see the beauty of others?

Back to the shoes. 

Balancing homeschooling, our home renovation, and all the great success I have been having via OMHG plus other projects has left me pretty wiped out. So I snuck out of the house to get my hair done before my interview with April of Blacksburg Belle. It had been months, I needed a hair cut!

Fluevogs have always topped my covet list- a symbol of success and abundance. Walking into the shoe store, and trying on these shoes in the 1/2 an hour before my hair cut, was an act of random synchronicity and impulse. After our Spark Retreat call with Alexandra Franzen and Dyana Valentine I was so open to magic of any kind. The shoes fit like a dream, and made me ridiculously happy for a material object, but I gasped at the price thinking there was no way I could afford them. I have been saving all of the money I make through OMHG for a site redesign to add more engagement for our community. How could I justify such a huge expense?

Then the sales person told me the story behind the name of the shoe…and you all know I have a soft spot for stories and women in business. These shoes just happened to be named after the incredible:

viola davis desmond, women entrepreneurs, african canadian entreprenuerViola Desmond was a true heroine and brave soul. An African Canadian from Halifax, she led the way towards equality for Canadian women of colour with beauty, grace, class, and white gloves. She was also a trail blazing entrepreneur and business woman, at a time when most women (regardless of colour) were considered inferior. In addition to being Canada’s ‘Rosa Parks’, Viola created the Desmond Studio of Beauty Culture and the Desmond School of Beauty Culture and was the force behind a Nova Scotian Black beauty industry that is still vibrant today. If there is any woman whose shoes I would be honoured to walk in, it is hers! Learn more about Viola’s story here and here.

I bought them, eek! Then I went and got my hair done. Blue and purple hair? Yes! I thought about Viola Desmond and the purple shoes and freedom. That night I wore my new shoes while April interviewed me. Even though Sela made me run away from the interview to take her to the potty (twice) and Ila snuck out of bed and interrupted us, I felt strong and awesome. The next day I got all dressed up and had my mama take some quick pictures before Chris and I had a date so I could take my new shoes for a spin. When I got home I asked Twitter & Facebook friends to help me choose a new headshot-I never expected over 80 people would reply, and so beautifully!!!! I am honoured by how much love I receive here. It makes my fears seem pretty silly and all in my own head. Just like I talked about with April in our interview…synchronicity?

women entrepreneurship

If the shoes make the woman then I am ready to step into my power, honestly, and with integrity. Not by making it about me but by seeing myself as worthy of all the lovely emails + a pair of nice shoes, and pretty pictures. And by accepting that I can be successful, ethical and community focused at the same time. These shoes were made for walking straight into a future that is radiant and full of wonder- I am so grateful you are all coming with me! Cheers to us all sharing our loveliness with the world and stomping on the limitations we put on ourselves.

Now I feel like I can talk about ethics more authentically-here I am friends! My face (no Photoshop!)! My feet! My struggles! My hopes. My very own about page. And if you want to see me up close and personal go check out my live interview with April of Blacksburg Belle right here, or better yet, come hang out with me (& my pretty shoes) in New Mexico at Spark Retreat!

If you made it through this huge post that was all about me, thank you, now it is your turn! Have you ever felt like this? Afraid of owning your own awesome? Not seeing or valuing your success? Caring for others but not yourself? Hiding your true self away because of shyness or self-doubt? Please feel safe to share your story in the comments, I’m right here with you! 


  1. Tacha Reed says:

    Thank you for this lovely post; as I read the first part I thought “this could be me!”

    I’m constantly reminding myself that I need to be my own biggest fan. Today marks one year since I bought Sylvia, the vintage airstream that now houses my own shop Flying Cloud Boutique. So many amazing things have happened in my life this past year and up until now I hadn’t really looked back and gone over everything. Thank you for reminding me to sit down and look back – my whole life has completely changed and I’m now living my dream – I deserve a pat on the back for that!

    Sometimes it is hard when you’re your own boss. Without having someone to check in, pointing out my own progress, I sometimes miss out celebrating all my accomplishments. So thank you for making me think – and I’m so glad you are sharing a bit more of yourself (love putting a face to a name!) and celebrating you own accomplishments!

    • Jessika says:

      Where do I even start replying to these wonderful comments! There is always the sense of nervousness when posting something like this-what if no one replies?! Your responses are just what those butterflies needed!

      @Tacha-Thank you for your comment! I must make it up to hang out with you and your Airstream (did you name her after Plath-one of my favourite poets) & see your shop in person. You do deserve a pat on the back from yourself & hopefully from others who support you, way to rock your dreams! If you are ever in Halifax be sure to tweet me, would love to meet up:)

      @Mama/Stephanie-Your power is waiting for you, she hasn’t gone anywhere & is infinitely patient. I believe this with all of my heart. Keep stretching! I am so very lucky to have this community but I wouldn’t have found it if you hadn’t taught me the value of community & how material things are nice but what we build with our hearts is more important. I love you! And thanks for sitting on the kids while I bought pretty shoes & got my hair did:)

      @Isa-Its a dichotomy, I am fierce but also fiercely shy/self conscious. I would never have thought you to be shy either-you are so brave & wise & full of insight. Goes to show that what we project is only a piece of a larger picture. So thankful to have your support & to support you in our journey!

      @Arianne-Thank you! It is always easier to give good advice then to take it!

      @Angela-First big giant hugs to you! If any community can help you find your confidence it is this one:) I hope you can join our #omhg Twitter chats some time & connect with others who will help you celebrate yourself! Its not an easy path by any means but it feels good (and terrifying as all leaps do!).

  2. Stephanie Douglas says:

    Fantastic, phenomenal and brilliant post – It made me cry because it was like reading an autobiography.

    Except that you have caught yourself in time. I’ve had a lot more years of trying to play smaller and have shrunk myself so much there is nothing left. Maybe if I could just stretch a little bit, I could stretch myself back to me.

    You are lucky to have such a strong community like you have here, and your community is lucky to have you as a member.

    You are a brilliant strong woman, but also a complete woman with all the vulnerabilities that a full person should have, but should not have to hide or be ashamed of.

    Celebrate your completeness because you oh so deserve to have the very best that life and yourself have to offer.

  3. Isa says:

    I never would have imagined you shrinking back from anything! You come across as fierce, strong and beautiful (the best combination!).

    I am incredibly shy but I’m learning to focus on my passion for my work instead of letting fear take over my life. So yes, I’ve been there and I told myself no more. I honestly took charge of my life and told myself it’s ok to have fears as long as you don’t let them hold you back. I’m glad that you have found your way of taking steps to show us all who you really are.

    @stephanie Your comment made me cry. I know you are an amazing woman, you must be as you raised Jessika, a strong and powerful community builder. I truly hope you can get back to being yourself. It’s never too late x

  4. Oh my gosh Jessika, I’m sitting here bawling as I read this post because I felt like I was reading one of my own journal entries!!! How amazing and selfless of you to share your truth and be so transparent with all of us. I so want to step into myself and my success because it’s been 5 yrs since I left Corp America as an admin to pursue graphic design and I’m still scared straight! I know it’s now or never, just trying to find the confidence to step out there. Thanks for sharing. It truly made my day. Angela

  5. Helllll to the yeeessss! Oh god, Jessika you had be crying by the time you said “stepping into your power.”

    I often feel the same way – coming across as stronger than I feel; people are surprised at how shy or nervous I am about things. I’m the first person to say to others “be kind to yourself” or “you are stronger than you think” and then often feel like a failure when I don’t live up to my own expectations.

    I’m learning as I go, especially as my business grows and I am putting myself out there more and more publicly. But even more than that, I feel like I am having epiphany after epiphany – the more I put myself out there AUTHENTICALLY and true to myself, the better things are – my wellbeing, as well as my business. But the more I expose the true me to people, the easier it is to sneak back into my corner and hide.

    I keep putting myself out there though, and am proud of that. I need to just say “f*ck it” whenever I feel nervous about being amazing, and just jump. I need to remember that everytime I’ve taken those jumps of faith, I’ve felt the safety net of friends and colleagues and love from everywhere.

    So, hell yes, I’m so excited to meet your shoes in New Mexico, and I’m so flipping thankful to you and everyone out there who bares their soul. It helps the rest of us feel safe doing it too.

    Tania xoxo

    • Jessika says:

      @Tania We are going to have such an amazing time in New Mexico! I had an hour or two when I almost didn’t publish this post bc I felt that it might make me less credible if I show that my superhero cape has some holes. Then I said F*** it too! I am whole & broken just like everyone:)

      “I’m the first person to say to others “be kind to yourself” or “you are stronger than you think” and then often feel like a failure when I don’t live up to my own expectations.” YES! While nurturing/loving others is so good we forget about how that love needs to come from a place where we are also happy and fulfilled. I think those of us that are called to being of service are most often at risk of draining our reserves. I know that I often give more then I let myself receive, not because others don’t offer, but because I don’t always allow myself to accept.

      I can’t wait to curl up on a cozy couch with you & have ourselves a loooooooong chat!

  6. Sarah (mrsgryphon) says:

    Jessika, you are beautiful and strong in all the best ways. Thank you for sharing your struggles and triumphs. You’ve made me think today.

  7. Jessika,

    Wow, how lovely. Thank you so much for sharing your story. It was a little over a year ago that I discovered your blog and I have been loving it ever since.

    It is hard for me to put into words what your blog has done for me and my confidence. When I am feeling down and out, I seek this blog as I know it will bring a smile to my face and a bounce in my step (especially if I am rockin’ an awesome pair of shoes. fabulous purchase indeed!). It is rejuvenating – my “happy place” as my 4 year old would say.

    The Spark Retreat looks amazing! What an awesome time. I look forward to all the posts related to it!

  8. Cutelicious says:

    What a moving and lovely post! Thank you so much for writing it! And yes, I feel just like you described ALOT and most of the time!!!
    I also have been told more than once (or twice) to laugh not as loudly … I can seem very confident. But deep inside I struggle with so many things. I do believe in myself – but if people ask me what I plan to do in the future I never tell them about my ideas and plans as I am afraid of them laughing about me. In a way I would love to just be able to be myself – but yes, I do stick out! 🙂

    But in the end I actually believe sticking out is alot more fun than always fitting in … for some reason I always admire others that stick out. But I kinda forget to admire myself once in a while …

    Your post was really touching! Big thanks to you for writing it!


  9. Hello Jessika! Thanks so much for sharing the heart of you in this post. I used to hold back my ‘bubbles’, my exuberance, and yes, my loud laugh. Now I hold myself back by telling myself I’m much too old to grab the gusto for my little business (Felt On The Fly) and so I toy with it a bit and don’t allow myself to dream big and attack a plan for success like I could.

  10. There are a boat load of awesome posts here on OMHG, but Jessika this one is my favorite by far! So many have mentioned how they feel like it could be them, and I thought the very same! I am so freaking proud of you for opening yourself up and spilling your (beautiful) guts to all of us. This IS exactly what I need & wanted when I posted on my blog just a few days ago, “I want the truth- The plain, old, slap in your face truth. The truth about me and my flaws. The truth about my good & bad. But also the truth about everyone else.”
    Thank you for sharing YOUR truth. Here is mine:
    I’ve been looking in the mirror a lot lately, the kind where you stare at yourself and wonder if people see the same thing you do. The flaws, the insecurities, the stress lines, gray hairs, the crooked smile.

    Or do they focus on something else. Do they see that fire burning in my eyes, the fact that I sit up straight and talk loudly- even when I’m unsure of myself. Do you notice my blue shoes?

    I want you to see all of that. I need you to know that I have faults, I make mistakes, I sometimes fail. I’ve put myself in a box. Those things help to define the woman I am. The mom I am. The business owner I’ve become. ALL of these things help feed that fire in my eyes. When I’m wearing my blue Desmond shoes and trip on a curb, you bet your ass I’m going to stand right back up with a crooked smile.

    • Jessika says:

      @Jenelle-thank you for these truths, they are so close to mine! Do you ever listen to Ani? I think you would appreciate this song & lyrics: I was so moved when I heard this song for the first time as she was my teenage heart warrior heroine-these fears are ones even the strongest of us battle. That girl in the mirror can be so harsh and critical, but what this community has truly taught me is that what I might see when I look in the mirror is not what is picked up by those who really see me, that critical girl has no place here…and she can’t withstand the power of Fluevogs!

      It is also funny because I find confident women with their grey hair & crooked smiles & burning eyes so much more beautiful and intriguing then ‘typical’ beauties or young women (even though they have their own beauty). There is such power in owning our scars and flaws (those that can be seen & the deeper invisible ones too), we all fail/fall/falter, but my biggest hope is that none of us need to do it all alone. You are seen & loved & beautiful. Know this!

  11. Geri Jewitt says:

    What a wonderfully brave post to share with everyone! It’s not easy to not only look into yourself that hard, and harder still to embrace who you truly are and who you’re meant to be!

    And then you went and bared all of that – for us… your community.

    All I can say is WOW.

    Keep up the good work, Jessika – you are truly inspiring!

    • Jessika says:

      @Geri Thank you friend! I figure I can’t expect you to be open & honest with me if I can’t open up in the same way. Thank goodness for spaces like this where we can share the dark as well as the light:)

  12. Grace says:

    What an awesome post. This hit me at the very core of my heart. Freedom truly comes when you are being yourself and not hiding–afraid of how the world might react towards you. Sometimes, when we truly let go and be ourselves–we find that the world welcomes us with open arms.

    Thank you for sharing your thoughts.

    • Jessika says:

      @Grace “Sometimes, when we truly let go and be ourselves–we find that the world welcomes us with open arms.” Yes! Yes! Yes! WHen we are shrinking we call people to us that reinforce that smallness but when we open up to our true selves then others who will celebrate us seem to come out of the woodwork!

  13. Bridgeen says:

    The topic of this post is so important! And like some of the other commenters, I was tearing up a bit too. I have been thinking much the same thoughts recently, about how those who appear confident are not ‘allowed’ to be vulnerable too. And it can be so hard to express your vulnerable side when it’s not what people expect but you did, and better than I could have.
    It’s so so important to ‘own’ your own image, your sense of style, your hair. A good head shot can do wonders for your confidence. You should never be ashamed, or afraid to look good.
    I’m new in the crafting world, and struggling to find and ‘own’ my place in it, what ever that might be. But i’ve found this blog nothing but encouraging and helpful, and I’m especially enjoying the current emphasis on ethics.
    You deserve to be proud of what you have made here.x

    • Jessika says:

      @Bridgeen Thank you for this wonderful comment! It is so true that sometimes the more confident you appear the less vulnerability is allowed or help offered. Which makes it more difficult to ask for help & the cycle repeats. I feel so lucky to have this community that doesn’t expect me to be more then I really am & is willing to help out when I allow myself to accept. I think we all struggle to find & own our own place in our communities I hope you visit us often since we are on the same journey too:)

  14. Tina S says:

    Magnificent! I spent too many years trying not to laugh so loud, be so excited, act so happy, speak so frankly and smile so much. I finally figured out that God made me the way I am for a reason so I’d better just get on with being myself. Once I got used to that idea I forgot about wondering what others were thinking about me and started enjoying my life. If I fail, who cares? It’s better to try than sit on the sidelines of life and never experience anything! Gals like us are the ones who truly embrace life and all it has to offer. Sure we experience sad and tough times but we also get to have the most incredible thrills and happiness. People have asked me why I’m so happy all the time and my response is because I am fully me. Speak your mind! Do what feels right! If you feel like hugging someone, do it! If you want to laugh out loud, go right ahead. So people may make fun of you or whisper behind their hands about your loud laugh or how you always tell people honestly (with tact) what you really think. Who cares??? I’d much rather be living my life than hanging back, constantly worried about what other people think. If I offend, and sometimes I unintentionally do, I always apologize and explain my thought process. No one has ever held that against me. And they know very well that if they ask my opinion I will give it…so get ready. I am a gloriously made child of God. We only get one chance at life. Celebrate!

    • Jessika says:

      @Tina-I so fully agree! I have never been able to shrink myself to the point where I don’t speak my mind, give people big squeezes or generally be crazy exuberant & full of muchness…but even though I was still ME I had started to feel like maybe the reason I stuck out so much was because I needed to change. Thankfully I found my community of other wild, wonderful, larger then life (but still vulnerable) women + some men too who can remind me like this that who I am is just big enough:) Thank you!

  15. Chara says:

    Love this post! How easy it is to smallersize ourselves and how difficult it is to supersize ourselves back up. And then how gorgeously amazing it is when we do supersize ourselves and be the “me” we are meant to be.

    It was lovely to read this post, as I have been thinking similarily. I am trying to remind myself to push past the fear of what i think will happen if I allow myself to be big. It is possible I will trip. But it is possible I could fly. It is possible I will croak But possible I will sing the most gorgeous song.

    I love your bravery in admitting that you have moments of self-doubt and unsuredness. In this age of digital connections (which can be fabulous), it is also so easy to judge ourselves in comparison to others that we “know” or know of in our on-line worlds. Everyone else seems to manage doing it all, know what they are doing, have little self-doubt, keep their businesses and home fires burning with such finesse. The braver and more real we are about who we are and where we are and what is really going on, the more we learn to be empathic with ourselves and our own struggles (as well as be empathic and supportive of eachother).

    Supersize sista!

    • Jessika says:

      @Chara I just love you sister friend! And that you live close enough we can actually hang out & make things happen together! How true it is that we judge ourselves based on our perceptions of others. I get SO MANY emails asking “how do you do it” and I always reply as authentically as possible: I don’t. I just juggle my failure around from place to place. Some weeks I rock as a mama & my emails pile up then some weeks my business is on fire & I don’t remember to eat until midnight. But I forget that other women have the same exact struggles sometimes and start thinking about how if I was more like….I would be more organized, my house would be prettier, my kids wouldn’t scream at me. All untrue but still real at that moment. Hopefully by sharing my own messy life others will realize & share theirs & we will all feel more instead of less:)

  16. Joy says:

    Big huge hugs and so much love to you, Jess! You have always been such a huge inspiration to me. Thanks for sharing your heart…

    And, I just love those shoes.

  17. Jummy says:

    Thank you for this post, Jessika. There’s something about reading about you being your authentic self that encourages conversation and that is what community is all about.

    I’ve struggled with confidence in my ability to start an online community (both the logistics and the technical know-how required) and as a result don’t feel particularly successful online, despite having been a blogger for almost 10 years in various place.

    I would like to step into myself and own who I am completely. I would like to be successful and make all these dreams in my head come true.

    Thank you for inspiring me with this entry.

  18. Melissa says:

    @Jessika – I was not aware of the scholarship contest. Thanks for bringing it to my attention! Good thing I took a couple of days off this week. I need to get crackin’ on my entry before the deadline!

  19. Coral Lee says:

    Loving your photo on Twitter – so nice to see you. I wrote a post this week about how often we refer to ourselves as “just me”.

    I think we are often very supportive of others, maybe in a way we would like to feel supported. Even when we are doing great things for ourselves, we lack the confidence to enjoy it or pat ourselves on the back. To say “yay, you”.

    So courageous of you to lift the curtain and show your true feelings on this – you are not alone in feeling like this.
    Big hugs – Coral xo

  20. Stacey says:

    And this, Jessika, is why you are such a wonderful influence to so many 🙂 Your writing is very moving & your story is even more so… it is wonderful to see & read.

    Like so many people – not just women, but people in general – I’ve been told I’m too much this or too little that. It’s a challenge to work past the expectations of others – no one is perfect and everyone is imperfect. It’s a lesson that so many of us need to learn and be constantly reminded of. What we also need to remember is that we – ourselves – are the ones who choose to be influenced one way or the other. Or do the influencing ourselves.

    As an introvert and stubborn word-I-won’t-use-here, it’s hard coming to a point where I can be myself and not alienate (or offend, thanks to some of my language) people. I’m working on breaking out of my shell – I wrote a post yesterday about being myself and if people don’t like it, too bad – but it’s hard. But it’s only as hard as I want to make it.

    Jessika, you are a crucial member of this little community we’ve got going on here and I thank you for what you do and what you stand for. We may not see eye to eye on every issue, but you are doing amazing work. Keep it up! And enjoy those gorgeous shoes!

  21. wow. i found you through someone’s fb post, so this is my first visit to your blog, and i’m hooked! thank you so much for this article. i could have written it, all except…i’m still working on stepping into my power. thank you so much for the inspiration to do so!
    from a new fan… 🙂

  22. Jill B says:

    Thanks for sharing such a great story Jessika. I think my being true and sharing your feelings, you empower and inspire others.
    I think I will be referring to this post for a long time to come!
    I can truly relate to being “a tamer me” on the playground with the Moms…maybe I just need some purple shoes to give me that extra kick!

  23. Deanna says:

    Jessika, this brought tears to my eyes. Thank you. I’ve always always been the wallflower and being online has been a big adjustment for me. I still don’t write as often as I need because of my shyness.

    Thank you for shining your light on the idea that you can be shy yet laugh loud, smile big, wear funky shoes (always one of my weaknesses), and lead a wonderful community such as the you have nurtured here.

  24. Micheline says:

    I’ve read this post a few times never knowing exactly what to write here. I’m going to give it my best shot: What a great example of how to own what you have to offer without being a show off. It’s incredibly inspiring for people (like me) who have trouble standing in a crowd of people exposed, just as they are and feeling good about it.

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