Five years ago, Steph Hogeboom, found herself living in Kingston after falling in love with and marrying a Kingstonian. In that short time the native of Ajax has done what many take double that time to accomplish, she has established her own successful photography business that has taken her overseas to capture her clients’ milestone.  She’s now sharing the lessons she’s learned with local aspiring entrepreneurs through an intimate six participant workshop called Gather. 

Steph is the epitome of what I consider to be a “Boss Lady”! She pushes herself while encouraging others, she’s incredibly talented and she’s kind. If you have yet to see the moments she captures between doe-eyed couples and brand new adoring parents, check out her website here.

We recently sat down for a chat, read why she loves being a business owner in Kingston, what she loves about our special community and how she plans on guiding future creative entrepreneurs.

Keep up with Kingston: Why did you choose to settle down in Kingston and start a business here?

Steph Hogeboom: Kingston wasn’t really a choice. It kind of happened to me. Never in a million years would I have thought I would end up in Kingston. I moved to Kingston after school because of the age old story of love. My husband was here so that’s why I decided to move. And I think from the second I called this place home it continues to show me the opportunities it has in store for me. I think the biggest thing has been that I not only have Kingston as my home but two big meccas that I have been able to tap into as well, Toronto and Ottawa. It’s central between the two biggest cities I could ask for to run my business.

I think it has a lot to do with people really wanting to building a community here. But I just feel there is this tribe of – pardon my french – bad ass women who are  really doing an amazing job of raising each other up and I think it’s been a wonderful unexpected thing to build my business here. I didn’t think it would do as well. I just have to pinch myself that this is a real business and that this is happening. It was by accident but I would say it’s one of the most fortunate accidents that has happened to me. It’s quickly become the only place I could picture myself not only living but growing my business.

KUWK: You’re obviously very talented and love what you do. So what do you love most about it?

SH: It’s funny, I really thought I was going to be a teacher. Photography never came up ever. It’s just kind of something that happened and I rolled with it. I think that’s what happens when you plan, all your plans go out the window and then you roll with it. It wasn’t until I was a few years into it being a passion that I thought maybe this could be something that paid the bills. But I think for me, I’ve always been a story-teller, whether it’s been as an eight-year-old kid fibbing about what my brothers really did the night before or in high school going towards creative writing courses and I think it’s just a funny way that i’ve found my way of telling people’s stories. I don’t necessarily see photography being what I do forever. I always see myself somehow telling stories, working with people.

It’s kind of a vulnerable thing to be in front of someone’s camera, either you connect with them or you don’t and luckily I have been able to connect with more people than I haven’t been able to connect with. So it’s just the people I love. I love telling their stories, I love telling the relationship, no two relationships have been the same, no two weddings have been the same, no two families have been the same. So it’s incredible.

Coming to a new place, it’s a hard way to meet friends and new people and it’s just kind of helped me meet a lot of people and connect quickly with people as well. It’s a fun role because somehow you’re a go-to leader on the day if there isn’t an official go-to wedding planner and it’s a nice feeling when people come to you for advice whether it’s just in this moment, or just for these photos it feels good to be in that role for people.

KUWK: Would you say there is something special about working with people in this community?

SH: I think the thing about Kingston is that you’re really kind of routing for your home team. I’ve never met a band of people who are so loyal.  It doesn’t matter if it’s a group of high school friends who grew up here who are in Toronto but still call Kingston their home. No matter what sort of group I tap into there is just this hard, fast love of Kingston and so I think immediately — especially if I am working with a Toronto client or someone who has moved away but Kingston is their home — I have an instant connection. It’s neat.

I was reading on your blog and I had never thought of it before about how Kingston is like the Florida of the North and I think sometimes you get jaded if you’ve been here this whole time but as a newcomer, I see this wonderful melting pot. There’s a lot of art, a big artistic community here and it’s growing. It’s like the little city that could.

KUWK: Let’s talk about your new project Gather. Why are you starting it and why do you feel it’s important?

SH: So Gather is a big passion project for sure. I mentioned earlier that teaching was always the plan. So Gather really feels like an amalgamation of a lot of life events and a lot of things that have happened to me. It feels like the two greatest passions that I have ever — in my 27 years —  stumbled upon, merging.

It’s funny, I feel like normally quitting my job and starting this full time, I couldn’t sleep and I would be nervous. Launching my two associates to the world, I didn’t sleep. A lot of things have kind of led with nerves which is good because I totally feel that if you’re not feeling like you’re on the edge of your seat, you’re too comfortable. I totally agree with that.

There’s something about this that just feels right. And not to be too cheesy, it just feels like the perfect city to be doing this in, the perfect time. I’ve been waiting. I’ve really wanted to do this. The first workshop I ever went to was in 2013 and it was the first time I realized I could combine teaching and photography and I knew I had to wait, I knew I had to have the chops to back up that I was worthy of teaching this workshop. It doesn’t feel that I’ve achieved enough or that I am amazing enough, I just feel that the community that is backing me right now is enough. Whether I rise, whether I fall I feel that — again — there is this tribe of — not to single out women because I know that there is a tribe of incredible men in this city as well — but right now I just can’t help but feel this love from this community and it’s really gotten stronger in the last couple of months with meeting and forging these relationships. I think it’s just a mix of where I am in my career and the relationships I happen to be in right now that give me that spark to be like, “damn, maybe I can do it!”.

KUWK: What are you hoping that participants will get out of Gather?

SH: I think the biggest thing is the courage to know that they can do it. I think that starting a business can be a very scary thing. There’s obviously a lot of questions people have and I think if I can be someone who just like the people who came before me gives that gentle push just to say, “you know what, you can do it” then that’s what this is about. It’s to break down what I think are the scariest parts of making a business. To meet these ladies — I didn’t mean for it to be a bunch of ladies — but I am so happy that it is six ladies that I am going to be embarking this on for the first time. Take down the scary walls, show people that they can do it and also give them the gist that it’s going to be harder than they think but my god it’s going to be worth it. So give them the dose of reality but also give them the beginning tools to know that they can do it. I even know from the women I’ve talked to that they can do it, just emailing and saying “I’m ready” means they’ve got this. They just need someone to tell them that they’ve got it and I am totally willing to be their cheerleader. Not just for the day but to build the community forward and I think that’s what Kingston is really good at. The community factor. This is going to be the start of a little community that will hopefully filter into others.

KUWK: Less than a week after you’re call out and your session is full! How do you feel about the warm response?

SH: I said to my husband, “I’ll run it with two! Just get me two people and I’ll run it.” So it feels good when people are responding with something that you’re so passionate about. It feels like a weightily responsibility in the most wonderful kind of way that people believe in you and I want nothing more than to blow the socks off of the people who are trusting me with this and I think maybe it’s a sign that we should do some more!

KUWK: What is your advice for creative entrepreneurs?
SH: Take a workshop, obviously (laughs). I think more than anything you’re so much more capable than you realize and there’s been a lot of situations in this business where I’ve reached a stop gap and thought “this is it. this is where it ends” because emotionally, physically, mentally I don’t have anymore to throw at this.  I think I spend as much time on my business as I do at my marriage more than I do with my friends. It’s one of those situations if you let it stretch you and grow you, it will make you bigger and better. It’s usually in those times that you know it’s working. That’s when you’re becoming a better boss, a better boss lady. Not to discourage anyone — it’s scary as hell but it’s worth it.

Learn more about Steph’s workshop Gather.

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One thing I’ve noticed since being back in town is how Kingston has grown out of the old “Florida of the North” stereotype. Sure, there are a lot of retired people who choose Kingston but there are also a ton of young people making their dreams come true – from business owners to writers and photographers. And perhaps I am a tad bias being a woman, but I am proud to see many of them are women! So I’ve decided to interview these successful ladies and find out exactly why they chose Kingston to flourish and the benefits of living in such a close knit community. Click here to meet other Boss ladies featured in this series: