CREATING A CAREER THAT REVOLVES AROUND YOUR DOG (aka: the dream)
Only blue quoted text is the opinion of Jess Bolton (marked JB), the rest is my own.
Turning your passion into a primary source of income is the freaking dream.
Well, it's mine at least… And probably yours too.
I admire and take a lot of inspiration from those who achieve it.
A humble Instagram account dedicated to pictures of her re-homed, anxious pet whippet exploded during the pandemic, enabling Jess Bolton to create a monetisable brand and online community advocating for mental well-being and caring for challenging dogs.
Pretty cool, right?
JB: Basically, I was just kind of happily posting pictures of my dog to a very small audience. Then the pandemic happened, and I think that all of the things that Jess was worried about really resonated with a lot of other people, and it kind of took off.
Worried Whippet now stands strong with a collective social media following of over 250k.
Exiting mainstream employment to commit to her business full-time has enabled Jess to land partnership deals, write and publish a book and produce a podcast. Who knew that one sweet little whippet could create so much opportunity?
Jess joined us in October 2023 for the launch of her book Worried Whippet: A Book of Bravery.
JB: The book came out in September, that’s really nice. It's basically an illustrated picture book.
I got an email a couple of years ago from my editor at Harper Collins saying: ‘Hey, would you be interested in writing a book?’ And I saw it, and I thought like, that’s definitely spam. And then I looked at her email address which was @harpercollins.com and I, you know, burst into tears. [laughs]
So that’s been a whirlwind and wonderful. I got to work with an amazing illustrator and see how the publishing industry works. It’s been fascinating and exciting and seeing people now buying it for each other for Christmas is just like…
AH: That must be awesome.
JB: Yeah, it's really lovely.
After helping her facilitate this heart-warming event, which included a very pleasing amount of dogs, I was keen to invite Jess for an interview to find out more about her journey as a small business owner, learn of any challenges she’s faced and uncover her advice she has for those looking to run something of their own.
Please enjoy our favourite snaps from Jess’ book launch throughout this piece. (I took them, and I am very much bookable for any dog-themed event ever).
Bye bye burnout.
I asked Jess about the transition from mainstream employment to becoming her own boss; she shed light on the struggles she faced previously as an employee due to her neurodiversity.
JB: It was scary, I’d been planning it for a while and in the end it didn’t happen in the way that I’d imagined it would. I had a period of burnout, I got bought out of my contract. It wasn’t like I actively decided like: I’m at the top of my game and I’m gonna make this move.
I’ve got ADHD, so that was my fourth job in a row where I’d ended up feeling overwhelmed and panicked. So, yeah I almost kind of flunked out of mainstream employment.
I always did well in my jobs, but I always felt burned out by the end of it and just couldn’t keep going. It wasn’t intended as a power move, but it was the best thing that’s ever happened to me.
It was refreshing to hear Jess talk openly about burn-out and how, despite being good at what she did and yielding results, she still struggled and felt unhappy in her jobs. Unfortunately this is not an uncommon experience. That must go to show that there’s likely a fault in the environment, not the person.
One of the most attractive qualities in being your own boss, in my opinion, is creating a working environment that totally aligns with your mind and its strengths. There’s no need to squeeze into a society-shaped box that dictates your working life.
JB: I find that I very rarely struggle for motivation in this job. The approach that I’ve taken is rather than managing myself, like I would manage somebody else, I wake up in the morning and just lean into the thing that I’m most interested to do that day.
That was quite a deliberate thing that I did in the beginning: go where the fun is and see what happens. And it's so far kept me in good stead so I think that's how I’ll keep doing it.
I’ve done a full year now, and in another job I’d be unhappy by now. I think it's going really well.
too much of a good thing?
Interestingly, as a result of this joy and lack of burnout, Jess highlighted a caveat to this freedom.
It seemed that an unwavering input of passion into a job would, quite rightly, make it difficult to clock out for the evening. After all, if it doesn’t feel like work, how do you really know when to stop?
AH: What would you say is the biggest challenge you’ve faced since making this move to being your own boss?
JB: Regulating the way that I work. I work most evenings and most weekends, but not all weekend and not all day everyday. Do you know what I mean?
I’m like, constantly switched on. I’m not 100%, but I don’t take times where I’m properly away from my work. So I need to work out how to do that.
I do it because I’m interested and I’m engaged and I’m enjoying myself but it's still not good for me. I need to find ways to really detach myself from it. But it is difficult with social media.
Though enjoyment is of course not a negative thing, Jess’ awareness of her struggle made me realise that a lot of people might be facing similar difficulties.
Constantly being ‘on’ is a very real issue and could at times be misinterpreted as dedication or commitment to a role; but overworking can be tough to identify when you’re genuinely enjoying yourself.
Though I’m not a business owner, I have found myself viewing the world through an Anomalous lens and clocking in when I shouldn’t. This could (and has) looked like me pitching to someone I deemed a “prospective client” at a party whilst we’re both drunk…
It’s a joy to be so invested in something; but it is essential to find balance. If you find yourself deviating from a standard working day, it seems wise to set boundaries for yourself and try to make regulation a priority.
making a genuine impact.
Social media is a funny thing. It can create pure joy, and then wreak havoc immediately after.
Fortunately, Jess is one of those creators who appreciates the responsibility and influence that comes with a large following.
I’d automatically assigned Worried Whippet to the “safe space” category of the internet, probably because she talks openly about mental well-being, gives her audience a corner of the internet to share worries, take comfort and connect with people.
It wasn’t until speaking to Jess personally that I understood those things didn’t necessarily qualify an Instagram account as a safe space, and social media is quite a difficult place to label anything as completely safe.
JB: I think as much as I try, I don’t think I can claim it as a safe space.
I think that's the nature of social media: that it isn’t always that for other people and it definitely isn’t always that for me, as much as I want it to be.
So, I think rather than thinking of it in absolutes, I think of it as trying hard to get as close to that as possible.
That being said, whether she can truly claim the term “safe” or not, suffice to say that Jess is definitely making a positive impact and holding space on the internet for her audience to take time for themselves amidst the chaos of life.
JB: So I’ve always done a lot of check-ins, where I ask people how they are and they respond. The feedback has always been that it just gives them a moment in their day to think about how they’re doing.
I also have a thing called the Worry Box where I just stick a box up there and say like, leave your worries with us, go about your day. And that’s been quite extraordinary because people put anything and everything in there.
Making a positive impact on someone need not be life-altering and earth-moving; a simple reminder to take time for yourself and reflect can be all it takes to make someone’s day. For me, this is what the Worried Whippet is all about. Simple, small acts of kindness.
Jess and I touched upon the importance of holding space for others, and she valiantly shared some of her past experience in which social media was a massive tool in her healing process. It is easy to say that Jess is now paying her positive experience with Instagram forward as a creator.
JB: I went through recovery from an eating disorder in my 20s and social media is one of the things that had the biggest positive impact on me and that helped haul me out of that place.
Seeing people who were generously and very boldly sharing their bodies online - I wasn’t seeing diverse bodies through advertising, media, film, TV, whatever, but social media was a forum where that could happen. And I think it kind of democratizes people’s experiences in a way.
So, it's been really important to me in my recovery journey, and I like the idea that I might be part of that for somebody else.
CONSISTENT EXPOSURE TO SOCIAL MEDIA.
I can already guarantee I’m going to talk a lot about the drawbacks of social media in Anomalous Stories, but I really do believe it can be so toxic.
Though an online community can undeniably create warmth and camaraderie, unwelcome visitors can also be a feature of sharing parts of your life online. Jess is another creator who unfortunately has been on the receiving end of unpleasant messages.
AH: Social media can be a force for good, but obviously it has its drawbacks.
You’ve got quite a large following, you’re on what, 250k across all four platforms? Do you ever experience negative side effects from the limelight?
JB: With social media, for me it's not necessarily like things that are inherent to the platforms, but it's that you’re engaging with and essentially talking to in your comments and your DMs to so many people, strangers, every single day.
And inevitably, some of those people are going to be projecting stuff onto you that is not yours. They’re gonna be angry about stuff, having a bad day. So I do get messages that aren’t very nice to receive, I think a lot less on my dog account than my human account.
In addition, social media often exposes you to involuntarily witness negative news cycles or other unwanted posts. When your business primarily lives online, it seems that it would be quite difficult to effectively dodge this negativity. I suppose the key is to not internalise the energy it provokes.
JB: It makes it hard to look after yourself and look after your mental wellbeing.
When you’re on social media you can’t really pick and choose what you’re shown at any moment, like to an extent, it’s just gonna show up on your news feed so that's a bit difficult too.
THINKING OF STARTING YOUR OWN BUSINESS?
I was honoured to learn more about Jess’ honest experience as the leader of Worried Whippet; running a small business clearly has its own set of benefits and drawbacks, some that I hadn’t considered before.
I think we can all agree, however, that a career centred around dogs is a career well done.
JB: Start now. There’s no better time to start than now. And it's going to take you time to get yourself into the position that you need to be in to be able to leave your job. Think strategically about how you want to get there.
And, save. Money is the thing in the end that will enable you to make that move confidently. Like having a few months worth of cash put to one side.