Escaping the 9 to 5 with Kara Cahill

becoming an Instagram strategist with Kara Cahill

This month’s interview is with Kara Cahill. If you’re part of the One Step Outside community, then you’ll recognise that name because she is none other than our very own Community Manager!

Kara was working in a bridal shop when she applied for the role with me and, in less than a year, she has transitioned completely out of what was a full-time job to run her own business. Starting out by offering admin services as a virtual assistant (VA), she focused more and more on social media management and now coaches other VA’s on how they can get their business up and running just as she has!

Read on or watch the full interview below to hear more of Kara’s story.

Becoming an Instagram strategist

Kara Cahill was working long hours and weekends as a bridal stylist and in less than a year, she has been able to quit her job and now works remotely as an Instagram Strategist and Coach for other virtual business owners. Today, she loves her work, helping VAs, Social Media Managers and other virtual business owners with their marketing strategy so that they can book out their services and take their business full time as well.


1) At what moment did you decide it was time for a change?

Traveling has always been one of Kara’s biggest passions, and now her business gives her the flexility to work from anywhere…even Bali!

So in the bridal world, in weddings, it’s very much a customer service role, very customer-facing. You’re working with people one on one, and it’s very emotional – a lot of emotions, a lot of people, a lot of families that you’re always dealing with. So it’s very fun sometimes, but it can also get super draining too. It’s high-pressure sales and a lot of intensity, all the time. I was working full time, so it was sometimes 40 plus hours a week. It was every single weekend and I was working nights, very late nights, sometimes until 8pm if brides wanted to come back in – it was my job was to be there for them and be super accommodating. I felt like my life and the things that were important to me were being put on the back burner because of this job. So that was getting to be really tough; it was so draining.

I had just bought a new home with my fiancé, who worked a typical 9 to 5, Monday through Friday; then I was working on the weekends too. It felt like we would never catch each other – I would come home really late and then he would have to go to bed to wake up in the morning early. So we were on this different time schedule. I was missing family events and time with my friends, who were all spending time together on the weekends; and I couldn’t even be there for a friend’s bridal shower. And it’s those little things that you think are okay to miss at first, but then when you continue to miss them and miss them, it starts to be like… I don’t want this anymore.

I would have people come up to me all the time saying, “This sounds like the dream job, you’re playing dress-up and this is so fun! It’s so glamorous here.” And it was – it was beautiful, and it was fun. But when I looked at the lifestyle, I knew it wasn’t what I wanted. And I had thought it was for the longest time. I had gone to school to be an event planner, that was my path, and I had thought, “I finally made it!” And then when I made it, I realised: this is not what I want. I had asked for weekends, “Is there any way I could have a weekend off?” And when they finally came back to me and said the best that they could do was one Sunday off a month, I just couldn’t do it anymore. I couldn’t picture doing it for 30, 40 years – I had to find a new way.

I came across working online, and I didn’t even know this was a thing. I started following all these people online and they were working online, traveling while they work. And I wondered, “How are they doing this? I need to find a way to do this for myself!” So I just started researching.

Luckily, I signed up for a retreat in Bali – it was a social media retreat – and I learned from people that were doing it, who had online businesses. Within a month after coming back, I connected with you, Anna, and then the rest just kind of took off.

I started off as a virtual assistant, working online, and I grew my business just using Instagram; now, that’s what I teach others to do! And it feels so much better – I just couldn’t be happier with the way things turned out.

2) What was the biggest challenge you faced in making the change?

I think it was really scary to first decide that I wanted to work online and to start telling other people in my life that I wanted to work online. I had told my fiancé, told my mum, my family… and no one really got it. They would ask, “What does that mean? How are you going to make money from this?” So I think the biggest challenge was having to first believe in myself that, “Okay, I’m going to make this happen,” and then trying to explain it to other people who weren’t familiar with it, who were so much more accustomed to this 9-to-5 job world.

In the end, they were on board for anything – they knew I had to get out of that job, and they were very supportive. But getting people to understand what it was that I was then doing was hard. My job as a bridal stylist was a well-paid job, and I was very comfortable with what I was making there. But honestly you could have paid me all the money in the world and it wouldn’t have mattered, I wouldn’t have stayed there.

And then, just figuring out all the skill sets that I would need. A lot of things were pretty easy to transition to, but it did require a bit of training. I did have to invest in some things and some courses and that retreat, just to learn those skills and get my confidence up to where I could say, “Okay, this works now, I understand how to do this.”

3) Where did you get the support you needed to make it happen?

So when I started, I did the retreat in Bali and that was just kind of me going in, learning from people that were working; just meeting people that were doing what I wanted to do first and foremost. And just seeing, “Okay, these are real people that have similar experiences – I can do this too!” So that was really great, just to hear from others that were in a place that I wanted to be; and it was attainable. So that was number one.

Then when I came back, I invested in a couple of virtual assisting courses to get my skill set up – so I knew what a CRM was, I knew how to do email marketing, things like that.

Once I knew I wanted to transition into social media, I took an Instagram course. I was just learning all of these things to make sure that my skillset was up to where it needed to be. And then, I said, “Okay, I have a baseline for skills, now I need a coach.” So I invested in a coach and we started working together – just to have that extra level of support from someone who was doing what I wanted to do. And I could ask questions too, because there are so many things that pop up and I would have no one to ask these questions to. Especially in the virtual world, there’s no one among my friends or family who does anything remotely similar. So, if I asked them, “How do you do an email funnel?” they don’t know what that is! It’s nice to have someone to bounce ideas around, someone in the same area and field. That has been really helpful.

At first I was still half and half, so I was working on my business as more of a side hustle and I still had my other full-time income. So when I first started, I was doing lower-level courses just to get started, and it didn’t seem that scary, because I still had the other income coming in. Now, I’m still trying to level out my income, so when I do invest, it does seem a little bit scarier, but at the same time I know I need to do this in order to get to that next level. I just look at it as an investment, and anytime I’ve invested in myself, I have grown – both the business and me as a person. As an entrepreneur, I feel like you have to do so much personal work and self-development. So you’re never not getting a return on that!

4) What’s the best part of your lifestyle today?

Today, Kara loves helping other online business owners learn the Instagram marketing strategies that have helped her grow her own business!

So first of all, I just love working from home. It’s nice to be able to sleep in a little bit, and I don’t have to get dolled up for work and wear high heels every day! So working from home, from my yoga pants, sometimes my PJ’s is great.

But really, the best part is to have more time with my family. A couple of weekends ago, my fiancé and I just went out and got brunch on Sunday – and that was something that we had never done. It was so great to be able to do something so mundane, and we had the time to do it together and I felt so grateful for this. So there’s that piece.

But then of course also just doing something where I feel like I’m in the right place. I feel like I’ve found my passion; every day, I’m so excited to work on my business – and I’ve never felt that before. It’s been so nice to feel like I am exactly where I want to be. I can have the flexibility to travel, to pick up and go somewhere else. It’s been such a great transition.

5) What one piece of advice would you give to someone who is considering making a big career or lifestyle change?

My biggest piece of advice is: if you are unhappy where you are, it doesn’t have to be that way. I thought for the longest time that I was going to have to work at a job that was 9 to 5 – I thought that was just how it was. And I hated it, I’ve never felt so unhappy, and I was looking at other jobs and it all sounded the same. And finally I realised that there was another way, and there is something that you can do that’s outside of that box, that there is a way to do that, even though you might not feel ready to make the leap… I definitely wasn’t ready when I first decided to do this!

I remember not even having a contract for one of my first clients, but you just make it happen, and you figure things out along the way. The only way you can really get to where you want to go is just by taking those little steps. And it might be a little messy, it might not be perfect, but you just do it and you’ll learn and you’ll grow with each step you take.

So I would say just start before you’re ready and know that you don’t have to stay where you are if you’re unhappy. There are so many other opportunities – especially today, there are so many opportunities to have flexible work, or part-time work, or online remote work. And I think if you can open yourself up to the idea that there is a new way to do things, that’s really eye-opening.

This past weekend, I went to an entrepreneur’s event, and everyone was doing the same thing that I wanted to do; and seeing their success and seeing these people crush it in their industry was so exciting. To hear that, and be in their world, in their sphere, was, like, “Wow!” It shows you what’s possible for you. And I felt that these people were my people. And they’re just a couple of steps ahead of me – and you can get there too.

So it’s really just about being around people, surrounding yourself with people who are in a similar sphere. Especially online, it can get really lonely when you work from home – so try and find some networking events; even online communities, Facebook groups and stuff like that can be amazing.

You can find Kara on Instagram and if you’re a would-be virtual business owner then make sure you join her Facebook group, the VA Visionaries!


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