How To Survive Your Thirties Archives - Page 3 of 7

When the topic of my job comes up, people usually have the same two questions: 1) How did you transition from a day job to working for yourself full-time? 2) What’s it like talking about sex all day?!

I’m in the process of writing a post for you guys that shares my journey as freelance writer, however in the meantime I thought it would be cool if I spoke to some of my favourite sex-positive entrepreneurs, in hopes that they’d share some of their wisdom. I’ve featured products from Ohhh Canada regularly on this blog, so I decided to catch up with the CEO, Katrina McKay, to get her thoughts on sex positive entrepreneurship and what it means to live a sexy life.

What made you want to leave your corporate job to pursue life as an entrepreneur?

I was lucky to find myself jobs at very entrepreneurial companies at the beginning of my career and worked in an innovative field – marketing. Marketing is all about knowing your numbers, assessing risk and executing on brilliant ideas; and that’s really what entrepreneurship is about, too. At a certain point in my career, I just didn’t feel satisfied anymore… I felt like I could do more. Plus I’ve ALWAYS been an entrepreneur – for me it’s not a job, but a lifestyle, a calling, my purpose. I was born an entrepreneur. I was always that kid with the new idea on how to make a buck… always selling something from lemonade to greeting cards to tickets to a theatre show. When it came to a point where I felt like I wasn’t able to be myself at my place of work anymore, I knew it was time to take the ultimate career risk and go at it on my own. It took me nine months after making my decision to leave to ACTUALLY leave – I made sure that Ohhh Canada and my other endeavours were profitable enough to support themselves…and to support me!

I know you mostly as the CEO of Ohhh Canada (that’s how we met initially!) and as Kat the Sexpert from my Toronto Sun articles, however I know you have your hands in several entrepreneurial pies, so to speak. What else are you up to business wise?

I adore small business – mine and other people’s. Ohhh Canada combines two of my passions perfectly – entrepreneurship and sex. I get to help people “express their sexy”, and I get to be an example of others of what’s possible in small business. The “Kat the Sexpert” site and brand is a natural offshoot of Ohhh, but no longer directly affiliated – as I’m getting booked more and more in the US and internationally it didn’t make sense to have my brand of helping others feel sexier be exclusively part of Ohhh. Sort of related, I’m co-designing a line of leggings and lingerie with my mother, who is also Ohhh’s Warehouse Manager. She’s a costume designer and extremely talented seamstress… so look out for those leggings in 2015 with other lingerie pieces to follow.

I also run an international business growth consultancy. We call ourselves the “un-agency” because we don’t care about winning awards, and we’re not exclusively marketing-related. We’re about driving bottom-line results for the companies we work with. All of that falls under the KatrinaMcKay.com brand. We’re really choosy with the companies we work with, because my team and I (eight strong in total across all of my companies) become much more like an internal team than an outsourced solution and that means that our personalities have to mesh as well.

Lastly I am a business coach to a roster of extremely talented entrepreneurs both involved in sexy businesses and non-sex related businesses. This is something I am very proud of – I love being a small part of the success stories of others. I work with entrepreneurs one-on-one to help them achieve the next level of success. To name just a few of the amazing business I’m involved in – Brass Vixens, THEIT, Elixir, Flores Boticario, Carmen Rachel and many more (too many to mention here). Coaching is really fulfilling – I get to help others avoid the stumbling blocks I encountered with my own businesses! Coaching has also led to a lot of speaking – particularly on how I left my 9-to-5 to strike out on my own and how to build your small business brand. Sidenote: I was always told I couldn’t talk about sexy stuff AND be taken seriously in business. Good thing I ignored all my naysayers – and hopefully in sharing my story with you we’ll inspire others to do that same!

Ok, so, whenever I’m talking to people about my writing career, one of the first questions people usually ask when I tell them what I write about is “Why sex?” What made you want to launch a sex-positive business/career?

I wonder if our answer is going to be the same here. I’ve always been the go-to girl for my friends. I went to a private very conservative board school for high school, and I would often have girls knocking on my door late at night to ask me questions about bisexuality and other issues… For example, I remember distinctly one girl really worried that she’d turned into a lesbian because she had a sex dream about her roommate (for the record I believe everyone should feel free to define themselves, or not define themselves, by whatever criteria they deem fit). Plus even as a child I remember always being really interested in sex and sexuality… curious as to what made people tick, and why boobs were considered sexual. I love sex – it’s a fascinating driving force in our personal and professional lives and we need to talk more about it. No one should feel shame or embarrassment about their sexual feelings or inclinations. Talking about sex is important. My business and my work as Kat the Expert, and this blog, all help in little ways to help others open up about sex and enjoy their sexual selves.

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Lately, I’ve been thinking a lot about the concept of lovers.

I know that the word “lovers” makes many of us cringe. Up until recently, I subscribed to Liz Lemon’s philosophy that the only place the word “lovers” belongs is in between “meat” and “pizza.” However, I’m asking you to hold back your dry heaves & bear with me for a minute.

I few months ago, I was out for drinks with a few of my girlfriends. My friend started to tell the group about an acquaintance of hers who, after turning 40, decided to completely re-think her approach to sex.

“She old me she’s done with the booty calls, one night stands and “friends with benefits” scenarios of her youth. Instead she’s decided to take lovers” my friend explained to us.

What followed was a discussion about the nature of “taking a lover” and how exactly it differs from the other options mentioned above. As it was explained to my friend, “taking a lover” is about an arrangement between two adults that involves enjoying each others company – both inside and outside of the bedroom – without the binding commitment of a traditional relationship. Unlike being “friends with benefits” which requires a pre-existing friendship, having a lover simply means you enjoy having sex each other and sometimes this comes with the added bonus of some quality companionship.

As I sipped my whiskey sour and mulled this over, I couldn’t help but think all of this sounded incredibly modern and sophisticated – like something out of a French movie. (Cue moody accordion music and cigarette smoke.)

“I think that’s what I’ve been doing with The European” I shared with them.

The European and I met almost a year ago when I decided to try online dating again. The first time I showed my best friend a photo of this guy her reaction was immediate: “Wow, Simone – he’s so not your usual type.”

Aside from being tall and handsome, The European is pretty much the physical antithesis of the kinds of guys I usually go for: he’s distinctly Nordic looking with naturally white blond hair and blue eyes. He’ll probably hate me for saying this, but without knowing him, you might mistake The European for (gasp) a Hipster. If you need a visual, think Alexander Skarsgard with geeky on purpose Elvis Costello glasses.

With that said, there was something that drew me to his profile. Although he was born in Canada, he’d spent most of his life living abroad. Amidst the (literal) sea of guys you usually meet online in Victoria, The European seemed smart, sophisticated and well, different. However, I’d be lying if I didn’t mention that I also liked how his arms looked in one of his photos.

We exchanged a few messages and a few nights later met for a drink at a local Oyster bar. My first impression of The European was that he seemed very serious, bordering on austere. However, a few minutes into our drinks and we were laughing and bonding over our mutual love of electronic music and the band Disclosure. When he walked me home, he kissed me outside of my house. I liked his lips and how he gripped me in his arms – gentle, yet deliberate and wanting. We made plans to see each other again.

There was a second date – this time at a local brew-pub (which I was completely overdressed for in my new Rachel Roy dress & cage heels) – and another kiss. Unlike a lot of my recent dates who just wanted to talk about Crossfit, I liked that I could have actual intellectual conversations with The European. I was looking forward to seeing him again.

However, a few days before we were scheduled to meet up, I received a text from him.

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Hello Skinny Dippers! I’m working on book stuff today, so my friend John Drake has kindly volunteered to step in with the next instalment of the Things I’d Tell My 20-Year Old Self series. John is my former writing partner, a fellow motorcycle & sex/dating/relationship enthusiast and one of the best dudes I know. I hope you enjoy reading John’s advice! Stay tuned for more dating updates, reviews & other goodies coming later this week!

During my last annual exam, my Doctor asked for clarification of my age as she flipped through my medical file. She laughed as I responded, “Do you mean in birthdays, maturity or mileage?” While I may not feel as sprightly at 33 as I used to after indulging in more than a few Old Fashioneds the night before, in my mind I am still 20 years old.

That was, until the trajectory of my life journey recently placed me in close proximity to actual 20 year olds, at which point I felt as wise as an owl and old as dirt. After being made instantly and viscerally aware of the stark contrast between the limited worldview of a vicenarian (20-something), I began to ponder if I was ever that immature and clueless, or whether current 20 year olds have just been pampered to the point of having far less intellect and life experience.

I may have found myself giggling like a schoolboy at the supermarket just last week when I came across a package of Hung Wang Asian noodles, however I also have RRSPs in the bank, I own a vacuum, pay my taxes on time and don’t have to be told to floss – all hallmarks of maturity in my books.

Just as I wouldn’t tell my six year old self that Santa Claus doesn’t exist, there is much that I would leave a mystery to thirteen years my junior John. I would most certainly leave out specifics; the who’s, the what, the where’s – all of the decisions I have made, even the poor ones, have taught me valuable lessons that I wouldn’t trade. What I would change however, are the times I hurt people I cared about or who cared about me, regardless of whether it was intentional or not. I would also like to set him up for a higher level of success, learning from my mistakes rather than from the School of Hard Knocks.

In that vein, I would offer my 20 year old self the following counsel, in no particular order.

Be Honest

The importance of honesty was instilled in me at a very early age. It was held in high regard, paramount in fact, among other honourable virtues like courtesy, ambition and cleanliness. While I have rarely been intentionally dishonest, we’ve all told little white lies or lied by omission. It may have been innocent, or possibly ignorant, but I know for a fact that I have inadvertently led more than one girl on in my life by not being honest about my intentions or where I saw the relationship going. One lovely girl in particular, who I considered merely a nocturnal recreation partner, unfortunately saw monogamy and likely matrimony in our future and I never did anything to convince her otherwise. Be honest with the people around you, but more importantly, be honest with yourself.

Don’t Waste Time on Fake Friends

Friendship is not easy and it is a two-way street. Even as you get older it can be difficult to discern which friends will stand the test of time, or which ones shouldn’t. When you are young your friendships are based on proximity and musical taste, but life gets far more challenging as years go on. I was convinced that I would have been the best man at my best friend from highscool’s wedding and yet by the time he tied the knot I wasn’t even in attendance at the ceremony. You will experience ups and downs. The friends who help lift you up when you’re down are the ones you want to surround yourself with. Your friends will become your family and your benchmark for success, so choose wisely.

Nobody Has It All Figured Out, Follow Your Own Path

Some people wait patiently until mid-life to freak out about not having their shit together, but on the eve of my 25th birthday I had a full-blown quarter-life crisis. Witnessing many of my friends lock down solid jobs, condos and investments had me reeling with self-doubt about following my unique and less financially lucrative career path. One such friend who was in attendance at that 25th birthday has achieved perhaps the most financial and material wealth of anyone I know. He recently admitted that he was miserable at work and was jealous of the freedom, experience and flexibility I enjoy in my work. It doesn’t matter how big your TV is or how many bedrooms you have, you won’t be happy if you aren’t fulfilled by your work. I’ve made a great salary and I’ve made peanuts, but I always followed my passion.

Respect Your Parents

Age and experience often bring perspective, which in turn provide context and greater understanding. But as my old man has said on several occasions, “Learn from other people’s mistakes, you won’t live long enough to make them all on your own.” You share common genetics and ancestry, learning from their experience and about your roots will serve you well in the future. Whether you learn a family recipe, not to put gasoline in a diesel car or that you happen to have a predisposition to certain health issues, listen to your parents’ lessons and respect the sacrifices they have made in order to conceive, raise and support you – through colic, childhood, adolescence and beyond.

Take Good Care of Your Body

Education is wasted on the young. Unfortunately, so too is the innocence and stupidity of youth.
Your body is by far the most amazing tool you will ever encounter but much like any appliance it requires care and maintenance. I wish I’d worn earplugs to loud concerts, I wish I had applied sunscreen more often, I wish I’d never tried smoking or eating fast food. These things don’t make an impact when you’re young, but they compound exponentially over time as you age.

Live Within Your Means

It wasn’t until very recently that I became even mildly financially responsible. I bought a sports car and a new motorcycle before I paid off my student loans, I used my credit card like an ATM and I took vacations I couldn’t afford. Long story short, I placed a higher priority on things than I did on experiences or peace of mind. If I was to do it all again with the information I have now, I would have been more frugal and enjoyed the simpler things in life.

The reality is that I could spout off advice until the cows come home, but I can say with complete certainty that 20 year old John wouldn’t have listened. He was invincible. Immortal. Unstoppable. With age, experience and opportunity comes pain, politics, cynicism, regret and self-doubt. Sometimes being an adult means carrying the weight of the world on your shoulders. I wouldn’t want to trade places with my 20 year old self and I feel like I have a great deal of valuable information to pass on to him, but something tells me he could teach me a thing or two about perspective as well.

What would you tell your 20-year old self?

I love those moments in life where you realize that you are completely different than you were a year ago, three months ago, or even three weeks ago.

Call it a moment of clarity, or what have you – but, I had one of these moments the other day. Maybe this has something to do with turning 34 a few weeks ago, or the fact that my three year anniversary of moving back to BC is steadily approaching, but I realized that I feel completely differently – about life, about love, about myself, about work – than I did three years ago. Heck, even one year ago. It was a really good realization, and to celebrate I decided to do something really big.

You guys, I threw out my leopard print pyjamas.

Those of you who have been reading for awhile, might grasp the significance of this. Up until a few weeks ago, I was hopelessly attached to my two sets of leopard print pyjamas (perhaps, a little too attached) – a reality that was well documented on Instagram & my blog. I’d sleep in them. I’d work in them. The only thing I wouldn’t do is leave the house in them. I started referring to them as my “freelancer’s business suit.” Things got so dire, that my family staged a pyjama-vention of sorts.

Although I was finally able to break my pyjama habit when I started to work out every morning, I kept the leopard print pyjamas in my drawer none the less (I had two sets that I’d regularly rotate.) I’d still wear them at night before bed, but that was it.

That takes us up to a few weeks ago, when I put on the older of the two pairs, bent down, heard a ripping sound and realized there was a giant hole in the butt. Luckily, I had another pair standing by! However, they only lasted about a week before the same thing happened.

Being the ever so handy person that she is, when I told my Mom about what had happened, she immediately offered to help me repair both pairs.

“Maybe, I could patch them. We could make the patches a giant bright pink heart if you want…wouldn’t that kind of match your blog?” she suggested.

There are a lot of things that wear out on a semi regular basis: running shoes, toothbrushes, nail files. I feel like pyjamas shouldn’t be on the list. If you’re blowing out the butt of your pyjama pants on a regular basis, you might have a problem. I should know.

“Mom, that’s really sweet but I feel like that would just draw attention to the problem and scream out…well, sadness. Besides, I think both of these pairs are just one rip away from being ass-less chaps.”

“You know dear, you’re probably right.”

“Also, I think it’s just time.”

So, the decision was made: I would throw out the leopard print pyjamas. To prepare for this event, I bought myself a new pair of very grown-up silk pyjamas from one of my favourite stores in Vancouver. However, then the summer got really busy and I simply forgot to dispose of the old pairs, until I opened up my bottom drawer today and promptly declared, “These need to go, NOW!” and dumped them into the garbage bin outside.

I’ll always have a place in my heart for these my well-loved, feline inspired former sleepwear but, they no longer serve me – both as physical items in my home, but also by what they represent.

The girl who lived in these PJ’s was trying to get over an emotionally jarring break-up while starting a freelancing career. She had an idea where she was going, but she was still afraid of a lot of things. She was afraid of really putting herself out there and getting her heart broken again, and feared that maybe she wasn’t good enough to really make it as a writer. She was also kind of lonely. She was happy to have moved across the country to start anew, but also longed for the active social life she used to have. The pyjamas provided comfort and acted as a security blanket to quell these fears. However, three years later I no longer feel like that girl.

I’m still afraid of things (who isn’t?) and yes, I definitely enjoy regular quiet nights in (featuring my new pyjamas and a steady stream of Netflix) but I feel like I’m on the other side of the phase of the one I described above. I go to the gym most mornings, I wear real clothes to work, I date and I have a busy social life. My life might not look that different to the outside observer but it feels different and that’s what counts.

In case you hadn’t already guessed, I’ve been on a downsizing kick lately. So, while I was still on a high from disposing of my old pyjamas, I did another big thing: I purged my closet and got rid of all the stuff that no longer fits me properly. This seems like a no brainer, but for me it was a big step.

As I’ve mentioned before, my body has changed a lot over the past three years. I’m no longer the size I was when I moved here but I’ve hung on to a lot of the clothes I used to wear when I still lived in Toronto – namely, a pile of size 23 and 24 jeans that I have long since outgrown.

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Given that I’ve been living with my Mom ever since I moved back to the West Coast, it shouldn’t come as a huge surprise that there isn’t a whole lot of sex happening in my bedroom these days (at least not with a partner.) Although I’ll forever be grateful for the opportunity to live with family while I grow a successful freelance writing business (I couldn’t have done it otherwise), it hasn’t exactly been great for my sex life. Not only do I live under my Mother’s roof, her bedroom is right next to mine. It’s not exactly a set-up conducive to sexy times.

However, I’d be lying if I said nothing ever happened in my bed. My Mom travels a lot, so there are times when I have the house to myself. And sometimes I date people. At 33 it often feels like my hormones are raging and I want to have sex with everyone & no one all at the same time. So, when the opportunity for sex arises sometimes you just have to roll with it and make do with what you have.

This is exactly what happened the first time Fitness Guy and I hooked up last year. After a fantastic date, I invited him inside and things progressed from there. However, once we were making out on my bed, I realized I was completely distracted by my familiar surroundings. While I should have been focusing all of my energy on squeezing my pelvic floor muscles or how amazing his ass felt cupped in my hands, there was this inner voice that kept saying things like, “What if he looks away from my boobs and notices that I have an extensive wooden monkey collection? Oh god, did I forget to hide my Muppet memorabilia before he came over?! Oh no wait, that isn’t Gonzo’s nose, that’s just an errant purple Dildo I reviewed last week.”

It was Fitness guy himself who pulled me back into the moment.

“Hey, there you are.” he said, as he tenderly held my face in his hands.

It was only when he forced me to make eye contact that I realized how distracted I had been. Our tryst was steamy and passionate, yet part of me couldn’t fully relax. It was silly, because at the end of the day I don’t really think Fitness Guy cared about what was on my walls or any of my strange collections of objects d’art. In fact, when we were finished he wandered around my room, thoughtfully looking at the artwork on the walls and eye-ing my book collection with admiration. If there was something about my decor that he found off putting, he didn’t let on.

With that said, I vowed that the next time I had a guy over I would make sure that my space was cleansed of anything that I might find embarrassing. Now, flash-forward to close to a year later, when I found myself in a similar situation with a new guy I was dating. When it was decided that we would move our make-out from the front seat of his station wagon into my bedroom, I asked him to give me a 4 minute lead so I could run inside and tidy up a bit.

Mainly I was concerned about Joe and Hammer (who at the time had been going through a particularly interesting week costume wise). So, I spent the next 3.5 minutes shoving everything (and everyone) into the closet as quickly as possible.

However, the same thing happened again.

Things were fine, until they weren’t. When my date noticed mid-makeout session that I seemed kind of distracted and asked, “What are you looking at?” I couldn’t tell him that it was this….

Sigh. Joe the Intern: always there when you need him and even when you don’t.

Whether it’s just casual or I’m in a relationship, I like my sex full of intimate eye-contact, playfulness and connection. However, for some reason I can’t quite get there when I’m in my own space. Instead, I find myself really holding back. The irony is that anyone who attempts to have sex with me in my own bedroom likely leaves with the impression that I’m a bit uptight and possibly have some detachment issues- which couldn’t be further from the truth.

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Interview | Living a Sexy Life with Katrina McKay of Ohhh Canada

On Lovers and Learning How to Hold On Lightly

Things I Would Tell My 20-Year Old Self #15 – John

On Pyjamas, “Aha” Moments & Buying Clothes That Fit

True Story: I Can’t Have Sex In My Own Bedroom

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