Anna S. E. Lundberg

Coach, Speaker, Writer

Fearless Fridays: From sales and recruiting to business growth strategy

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Fearless Fridays with Kelly RoachThis month’s Fearless Fridays interview is with none other than my own coach and mentor, Kelly Roach. Kelly is a former NFL cheerleader and had a hugely successful career in sales and recruitment before she decided to start up on her own in order to create what she most valued in her life: freedom, fulfilment and financial abundance.

There are so many valuable points that Kelly makes in this interview. She shares how she right away recognised the importance of having someone to guide her through the process and hired a coach a year before she even started her business; she talks about the importance of building a team so that you’re never alone as an entrepreneur; and she gives some powerful advice around showing up and doing the work to create a brand and an eco-system that will last for years – even when you’re not always seeing the results right away!

I REALLY recommend that you watch the full interview below (and keep an eye out for Kelly’s little entrepreneur in the making, Madison) and you can also read on for the highlights below.

Leaving a corporate job behind to follow your passion: From sales and recruitment to business growth strategy

Kelly RoachKelly Roach is the host of the top-rated podcast Unstoppable Success Radio, an International best-selling author, and the CEO of Kelly Roach Coaching. As a former NFL Cheerleader and Fortune 500 Executive where she was promoted 7 times in 8 years, Kelly brings a powerful combination of proven and profitable business growth strategies coupled with the mindset, wellness and productivity practices required to help entrepreneurs build a profitable business around a life they absolutely love. Kelly’s passion and purpose is in helping entrepreneurs around the world achieve exponential profit, sales and income growth.

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

I started off doing sales and recruiting for a Fortune 500 firm, and really worked my way up the corporate ladder extremely quickly. I was promoted seven times in eight years. I became the youngest Senior Vice President in the company, and I was managing 17 branches. I had a team of 100 people. Really what I was doing was a lot of what I do today, just in a different format. I was responsible for driving sales growth. My whole job was teaching, training, coaching, and developing people to one, believe in themselves, two, have the confidence, and three have the skills to go out and sell and market and build their business.

When I started my own business, I really took the best of what I loved so much and was so passionate about in that field and really channelled my energy into something that I felt was much more impactful and fulfilling to make a difference in the world, which is focusing on small business owners. For me, it’s very fulfilling when a business owner says, “I was able to pay off my debt,” “I was able to quit my job,” “I was able to pay to take my family on vacation.” One of my favourite success stories ever was when a client told me that after their first six months working with me it was the first time ever that they got to pay for all of their Christmas presents with cash.

It’s little things like that, that’s why I decided to do what I do. I know today that every business owner that I help, it’s a family that I’m touching, and it’s a relationship that I’m reinforcing because of that person now being able to have the freedom and flexibility to put their family first, which is my most important premise in my business. It doesn’t matter where you are today, whether that’s important to you or not, at some point it will be. If you start ahead, and you start working on that when you don’t need it, which is exactly what I did. I wasn’t pregnant with Madison yet. I didn’t have a daughter, but I was planning ahead for that when I started my business because I knew that by the time she got to be the age that she was interacting and kind of knew what was happening in life that I wanted to be a really present mom. When you plan ahead and you work towards your dream, and you set goals for yourself, you can make anything possible.

Kelly Roach coffee shop
Kelly realized that her core values are freedom, fulfilment and financial abundance.

The biggest thing was honestly quality of life. Getting seven promotions in eight years was my goal – and I really made the decision to go in early and stay late, and work on the weekends, I didn’t have to do that. The corporate world is a completely different beast than the entrepreneurial world: when you’re building your own business you build a team and you keep adding to that team, so you’re able to leverage your time. I don’t work any more in my business today than I did when I was a start-up, and we’ve grown obviously substantially. But the difference is in the corporate world every time you get a promotion, every time you take on more, you’re expected to just work more and more and more and more hours. There’s no correlation. You’re not actually building something that’s scalable, or that will allow you to then later reap the benefit and the reward of that.

To me, that was a very short-term way of operating. I thought, “This doesn’t even make sense. I’m not actually creating something that down the road I’m going to be able to leverage. I can keep getting promoted, but I keep having less and less time. Even though I’m making more money, I’m not accomplishing these things.” It was really just coming to a precipice of realizing that my three values were freedom, fulfilment, and financial abundance. I really had to do some reflection and I recognized that that is not available or possible in a corporate environment, especially in a Fortune 500 firm. You really can’t expect that in a job. I think you have to take responsibility to go out and create that.

Now what I will say is that I worked very, very hard in my own business to make sure that my team members are able to accomplish those three things, freedom, financial abundance, and fulfilment in their work. I do think it’s possible, but I think it’s very rare because you would have to have a business owner or a business leader that has that mindset of wanting to create that. In most companies or corporations, that’s not obviously, that’s not a priority. That’s not something that’s on their radar to create for people.

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

I think the hardest thing for me to learn as an entrepreneur is a willingness to fail publicly. That is very, very difficult, especially when you’re high D, type A, high achiever, which I know probably you are and so many other people listening. It’s very difficult to fail publicly, so that’s what holds most entrepreneurs back from achieving true success because unfortunately now with everything being done on social, you’re going to win or lose in front of everyone. You’re on a grand stage with everything that you do. I mean, I’ve had completely failed launches where I literally sold nothing. I’ve had webinars where I’ve had no one show up. I’ve had every failure that you could imagine as an entrepreneur.

It was really my willingness to say, “Okay, this is my starting point and now I’m going to do this over and over and over again until I nail it,” and be willing to fail publicly so that we could succeed and achieve greatness. That was the hardest thing for me, it was so difficult to do that. And even now, it’s hard. It’s hard being in the public eye with everything that you do. But I think you have to decide what’s more important to you, protecting your ego, or achieving the end result that you want. For me, I think to myself, “Okay, remember the end result, keep focused on your path.”

I think the other thing is that in every other facet of life we understand that you’ll have to practice and practice and work towards things for years, but then I think in entrepreneurship we expect that the first time we do something it’s going to be this magically perfect result. Then when it’s not, we think, “Oh, that didn’t work, let me go focus over here” – which is the worst thing you can possibly do!

My biggest message of 2018 for entrepreneurs is play the long game and you will be the only person leading in your industry. Everyone’s playing a short game right now, so if you’re the person that’s thinking about 5, 10, 15 years from now, the decisions that you are making will be 100 times more powerful than the decisions that your peers are making. Literally, the cream always rises to the top. You may feel like, “oh my gosh, I’m struggling, I’m scraping by right now, I’m barely able to get a client” – but if you’re making good decisions every single day, that will ultimately translate into you being the leader in your industry.

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

I’ve had lots of coaches and mentors myself. I always tell the story of the best decision I ever made when I started my business, which was that I started business coaching with Ali Brown a year before I started my business. That is how much I believe in coaching, in the power of coaching. I realized I could cut 5 to 10 years off just by doing it the right way the first time instead of trying to make it up as I go.

I had a background in business growth strategy and sales, and I still knew that there were immense differences between, for example running an online business and running an offline business. I can’t even convey the value in finding someone who is where you want to be and investing in coaching and training with them. I still to this day utilize so many of the things that I learned from Ali Brown in 2012.

I hear from people all the time that as an entrepreneur, you feel like you’re on an island, you feel lonely. Well, if you build a team and you get a coach, then you’re in a community and you have people who are rallied around you, all working towards a common goal. I never feel alone. I can say that I never feel alone. No one needs to feel alone. But the decisions that you make will determine if you’re on an island, or if you’re in the centre of this community with people having their arms wrapped around you.

I started off with a VA for one hour a week, and that was the start of my team. I think it’s very intimidating for people to hear ‘team’ because they’re thinking of investing $50,000 in a full-time person (or pounds, or whatever!). You know what I mean? Yes, that is the ideal, and that’s where you want to get to eventually, but that’s not where you’re going to start; that’s not where anybody starts. Just get started with some small incremental amount of help to allow you to focus on the right things so that you’re not getting dragged down into the things where you should not be spending your time and energy on.

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

Everything. I mean, I would say I’m at a stage now where years of making good decisions, years of planning in advance have come to fruition. The ability to have my husband home full time with my daughter, which was the number one most important thing in my life – I retired my husband so that Madison never had to go into day care – that’s my proudest accomplishment. Being completely debt free. Last year we paid off our house. We have no debt of any kind. Getting to take a lot of family vacations, spend quality time together, put my family first. Last summer, I took every Friday off. This summer, we’re doing a lot more trips, because Madison is older and we can travel now. I just think that after a period of years of doing the right thing, and doing the right thing, and doing the right thing, even when I wasn’t getting the results from it, it comes full circle.

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 for new entrepreneurs today is to focus on engagement-based video. That was not available when I started my business. There was no such thing as live streaming, and Instagram wasn’t even a thing at that point. I would say that is the best business breakthrough that’s happened in the past decade, and it’s free. If you’re a new entrepreneur starting today, you need to make your phone your best friend. You need to make your phone your best friend, and get on camera.

That is the biggest piece of advice I have for new entrepreneurs. It wasn’t available to me. Now with my second business that I’m just starting, everything we’re doing is engagement-based video: we’re live streaming every week, we’re doing Boomerangs, we’re doing stories…. And we’re seeing our audience grow faster there than my audience is growing in my coaching company. It’s because we’re leveraging the tools and technologies that are available today that weren’t available when I started my first business.

 

Find out more about Kelly at Kelly Roach International on Facebook and you can also follow her on Twitter and Instagram.

Fearless Fridays: From money to mountains

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Fearless Fridays with Sarah WilliamsThis month’s Fearless Fridays interview is with Sarah Williams. I stumbled across her in the She Podcasts group on Facebook, where I also recognised her from the Yes Tribe. Small world, with people living out big dreams!

After working in finance for eight years, Sarah quit her city job and spent 18 months travelling the world, climbing Kilimanjaro, backpacking around South America and doing a ski season, and using that time to help her decide on what she wanted to do with her life. She set up Tough Girl Challenges as a way of motivating and inspiring women and girls and she’s also the host of the Tough Girl Podcast, where she interviews inspirational female explorers, adventurers, athletes and everyday women who have overcome great challenges.

In the interview, Sarah shares how much she loves the freedom of how she can live her life now, as well as sharing some of the challenges. It’s quite a change to go from a ‘conventionally successful’ job in the city to forging your own path, and you’ll often find yourself up against some pretty strong doubts and judgements from certain people around you. She found incredible support in the online space and, despite the challenges, her advice to you is to “just start!” Read on for Sarah’s story or watch the full interview below.

Leaving a corporate job behind to follow your passion: From promoting investments to promoting strong female role models

Sarah WilliamsSarah Williams is the founder of the Tough Girl Challenged Podcast, dedicated to inspiring and motivating women and girls to get fit, active, travel, explore, have big adventures and generally live life to the fullest. An adventurer and endurance athlete, Sarah left a career in banking in London to complete several personal challenges including running the Marathon de Sables, walking the Appalachian Trail and climbing Mount Kilimanjaro. Sarah is now back at university and facing mountains of a different sort with her degree in Women and Gender Studies, whilst running the Tough Girl Challenges blog and podcast driven by her vision to see an increase in the number of female role models in the media.

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

It was very gradual. I’m a very positive person but it was a case of little things here and there. Week after week, it was becoming harder and harder to find faith, happiness, motivation and drive for what I was doing.

I was in a very fortunate position. I did have savings and I didn’t have any liabilities, so I could go and leave. I headed off to Kilimanjaro to go climb the mountain, which was amazing. I also spent time with family in Australia.

However, I do wish I had started Tough Girl Challenges when I was still doing my working job so that I could receive a regular income to build up the side hustle and learn everything I needed to learn about social media, editing and being an entrepreneur.

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

The big challenge for me is the financial side of things: it’s trying to make money from something I’m really, really passionate about. I moved back home with my parents and suddenly I’m a 36-year-old woman thinking “Am I doing the right thing?”

That’s still a struggle. I have these great days where I get nominated for an award, or I have the chance to share my story, and then there are really low days where you’re just sitting at a computer for 16 hours a day doing social media, trying to promote your podcast and your story, trying to get sponsorship and speaking gigs. It’s so hard.

I’m not complaining about it because it’s my choice and I’d 100% rather be doing this. I think a lot of people look at my life or look through Instagram and think “Oh, Sarah’s at the gym again,” or, “She’s out walking the Appalachian Trail,” or, “Oh, she’s doing X, Y, and Z” – but people don’t really get to see behind the scenes. That’s been quite tough.

It’s also adjusting your mindset about status. Working in finance in the city, or working for a big global corporation, people ask you “What do you do?” and you say, “Oh, I’m doing X for this bank.” There was a lot of ego involved. Then you have that stripped away and it becomes “Oh, I’m a blogger, I’m a podcaster…” You get very different reactions from some individuals. Some people are incredibly supportive but other people aren’t.

With my family and friends, I struggled with the suggestions of “Why don’t you get this job? You’d be so good at doing this,” whilst trying to explain that, “Actually, I’m really trying to make this work. I know it doesn’t look like I’m doing much, but this is my passion, this is my dream.”

There have definitely been hard times. Explaining to friends and family, trying to make money, living at home with the parents… My parents are amazing by the way! I’m actually quite lucky and very spoiled, but it is still a challenge.

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

Online, which has been amazing. I’ve got my own Facebook group called the Tough Girl Tribe, which is incredible. I think a lot of women sometimes feel isolated when they say, “I want to go and run across the Sahara Desert,” or “I want to do this challenge,” and they may not have friends and family around to support them. It was great to connect other like-minded individuals.

I also became a member of She Podcasts, an incredible Facebook group for other female podcasters to be able to ask those questions which you think are stupid questions (and probably are stupid questions). But sometimes you don’t know what you don’t know, and you need to ask, “What’s the hosting place? How do I get my RSS feed? And how do I link it in?”

I’m also part of a mastermind as well. I connected with three other women last year and we talk once a month. Everybody’s in a similar position or in a similar industry and able to share best practice and share their knowledge and experience and just get advice and tips.

But I definitely think it’s not the same as in real life. I think that’s one thing I’ve struggled with: I feel I’m losing my social skills because I’m so happy about what I’m doing. I just sit in my bedroom and work all day and go to the gym, I’m not having daily interactions or daily banter. Yes, I get it on Twitter and social media, but it’s not the same as physically talking to people.

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

Sarah Williams
Running the Marathon de Sables, a six-day ultra marathon in southern Morocco

It’s the freedom. It’s the freedom of choice that I can just do what I want to do when I want to do it. Last year, I headed off to the Appalachian Trail to do this big walking challenge – but my business was still running. I had pre-loaded all my podcasts and blog posts and I had a small team of amazing women who helped with my social media while I was away. I spent three months walking through the Appalachian Mountains in America and it was incredible. I think the freedom is amazing.

I think it’s having a choice too; I know all the hard work I put in now is going to bring rewards. And I love the fact I don’t have to work to a schedule.

Also, I don’t actually interact with people I don’t like now. I know that sounds really weird, but you know sometimes, in business environments, you’ve got to be sort of nice to everyone, and be professional. Sometimes you just don’t like them as a person and you think, “I find your attitude negative” or “You’re not my cup of tea.” Whereas now, 9 times out of 10, with everybody I speak to, it’s not about competition but about collaboration. It’s about working together and being supportive. It’s just a completely different dynamic, which is amazing. There are so many benefits.

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

Say to yourself, “No more waiting. Just start.” I really want to ram that down people’s throats! Just please start. Whether it’s that you want to start training for a 5K, or you want to get fit or healthy or go to the gym, find a new job or a new relationship – whatever it is, you just have to start. The first step is, unfortunately, the hardest, but then you build momentum and things start rolling and happening. You suddenly think, “Whoa, why didn’t I start this earlier?”

 

To keep up to date with Sarah and her latest challenge, as well as find inspiration for your own adventures, visit ToughGirlChallenges.com. You can find more information on the Tough Girl Tribe and listen to Sarah’s inspiring podcast here. Well worth checking out!

Fearless Fridays: From banking to promoting an active lifestyle

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Fearless Fridays with Annie RossI met Annie Ross on a paddleboard in the River Thames. At the time, she was “on her way out” of banking, although still confronting a lot of fears around what that could mean. Having realised that she wanted to do something different, she set herself a challenge of 52 sporting challenges in 52 weeks – and our paddleboarding weekend was one of those challenges.

The ‘Exerk Yourself’ challenge turned out to have a positive effect on Annie’s work, giving her job purpose during a time when she didn’t want to make any drastic changes. It also made her new project fun rather than having the pressure to start earning money and turn it into a business right away. Eventually, though, it also gave her the platform and the confidence to take the leap and focus on setting up her own business.

As Annie says, she’s now “obsessed with helping people get active”. I love her message that you don’t have to climb Mount Everest or take five months off to travel across the Americas. You can build adventure and fun into daily life. There’s also an element of bringing people together and using these activities to create a sense of freedom and purpose outside of whatever’s happening in your life, for example, when you’re considering a big career or lifestyle change.

Read on or watch the full interview below to find out about the thought process that Annie takes herself through whenever she has doubts, and the total flexibility that her work allows her these days.

Leaving a corporate job behind to follow your passion: From teaching to photography

Annie RossHaving been working at Deutsche Bank for five years, Annie initially set up Exerk to spend more time doing what she really enjoyed, which was staying active. Organising a year of 52 sporting challenges in 52 weeks alongside her full-time job gave her the confidence and the platform to eventually hand in her notice. Today, she’s building this into a more structured programme for corporate women who struggle to find the time to be active.

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

The final trigger was that I was offered a job via a contact that I’d made from a press launch, having been writing as a fitness columnist for the Evening Standard, who had picked up my blogs. I met this guy who, a couple of coffees later, said, “Let’s look into you working for us.” That gave me the confidence that I could get a job outside of banking – this was at a big sports company. I handed my notice in off the back of that being a possibility. While I was working out my notice, I finally realised that I didn’t want to go and work for this sports company because it was effectively just another office job.

I let myself have no plans for a whole two weeks(!). Then a friend of mine suggested a company called Impact Marathon Series, who were launching marathons around the world. It was this perfect combination of having freed up my time, wanting to speak more Spanish, loving organising sports events and bringing people together – and someone who was willing to fly me out to Columbia to do it!

London Marathon 2016
Annie running the London Marathon in 2016

So I ended up in Columbia two weeks after I quit Deutsche Bank, on my own for six months organising a marathon. It ended up not happening sadly, but all the work was put in and it was amazing. I did Columbia and Nepal with them, race directing Nepal and project managing Columbia, and there is nothing I would rather have done for my first seven months out of banking. It involved travelling, working, and engaging with people in a really different way, in a different country doing a different job. That gives you confidence by chucking you into different situations as you realise that if you can work in three different countries in the same year, one in banking, one project managing, and one race directing, you can probably do a few other things as well!

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

After the Impact Marathon Series work, I used my Evening Standard column to travel for a bit and write travel reviews. It was a natural decision after that to come home and be with my friends, my network, and create a business – calling a day on that nomad living in South America. Since then, it’s been weird, because you come back and everyone says, “Oh my God, you’re back! You must be back for a reason” – and the answer is, “Yes, but I don’t know what that reason is yet.”

There has been a lot of excitement but also not knowing who you are anymore. Before, it was, “I work at Deutsche Bank, I did this, I did that” – not knowing what I was doing now made me feel really fidgety and anxious. Not having a purpose was really difficult for me. Every three weeks, I’d get really excited about another idea, I’d go full on into it and I’d meet with HR companies from big banks to talk about their corporate wellness stuff, for example… and then something would happen, and I’d just go off the boil a bit. Then I’d pick up the next idea and run with that.

That was tiring for me and it was tiring for other people. It took time to step back and stop putting pressure on myself, to give myself the space to commit. I signed up to a marketing seminar, and it all kind of unravelled like a big knot that was there in my mind and my heart, and gave me a clearer path to what I’m working on now.

It’s weird as you’re only answerable to yourself, especially for someone like me who expects a lot and puts a lot of pressure on myself. There were days when I felt like Deutsche Bank had been a really easy lifestyle, in comparison! So that says a lot about how low I felt at various points.

You have to stop yourself every now and again when you find yourself on the Guardian jobs website! I still have those days when I think, “Let me just see what’s out there, just in case.”

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

I went through the process of asking myself, “Should I go and get a job? Should I just go back into banking and make life all rosy and salaried again?” So you sit down and you ask yourself questions: “Is it because you want money?” In my case, “No, my insecurities are not around money.” Then I would ask, “Is it because I’m lonely and I want to work in a team again?” “No, because I can engineer that into my life.” “Is it because I want to be learning in a different way, being put on education courses by the company or just learning from other more experienced people in the team structure?” And again, “No, I’m doing enough courses, I’m doing really interesting things, I can say yes to anything I get invited to at the moment if it fits in with the strategy…” So I was able to rule that out.

I’m also a big believer in the power of people. I have no qualms about sending off an email to any company or person that I think looks interesting. That has led me down some awesome and has been my number one thing in that respect. It can seem like there’s a lot that I’ve done on my own, but behind that you’ll find other people’s advice, ideas or even just a chat over the phone.

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

Total flexibility. It’s up to you to fill your time, which is a beautiful thing. In the corporate world, our time is filled by other people, our diaries are manipulated by our bosses, by our team assistants, by our colleagues, by our friends in the evenings… One of the main reasons that I wanted to step back from London was that to meet up with a friend, we were looking four weeks ahead! Now, flexibility means that I can give more time to friends, more than just between the hours of 7 pm and 9 pm one night every four weeks. I can say, “Hey! I’ll pop by and see your new baby,” for example.

I do have to be careful so that I set limits on the amount of work I do. And, although I said the power of people was the biggest support for me, there is also the problem that you can be too “yes-y” – you can end up having all these calls all day that interrupt your concentration just for the sake of having a call. I am very easily swayed so if someone comes over here with a really good idea, I will spend half the day considering that, before pulling myself back on track.

There’s a book that I love called The Art of Essentialism: The Disciplined Pursuit of Less by Greg McKeown. Life is about trade-offs, and if you want to build something new into your life, you have to get rid of the fluff. Every now and again, you just need to take out the stuff that isn’t working for you anymore, get rid of it, and work out what you really want to be successful and happy. Otherwise, everyone else will chuck their old laundry at you!

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

The thing I’m trying to tell myself – I don’t know if it’s advice – is to take life less seriously. I think if you’re anything like me, you put a lot of pressure on making the most of each moment and all that media around us reinforces that that’s the way we should be living. But if you’re naturally someone who does that, it can mean that you don’t actually enjoy those things. You want to enjoy the ride!

Hopefully, that’s a nice reminder to people who are moving out of the corporate world and into the other side of things, which is more volatile, can be just as stressful, and is more rewarding but in very different ways. You just need to enjoy it and be curious: “Oh, this is a new way of having a conversation, or of being paid – interesting!” And then you can reflect on that later. But overall: take life less seriously!

 

Since we spoke in the interview, Annie has continued to evolve her project and made the decision to launch her programmes under the existing umbrella of Exerk. You can read more about her programmes to help you build an active lifestyle “that can survive life’s twists and turns” on her website and follow her on Twitter and Instagram.

Fearless Fridays: From Escape the City to escaping the country

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Fearless Fridays with Jay DikeIt’s a short month, February, and so it’s already time for our next Fearless Fridays interview! This one is with Jay Dike, who had just popped over to Boulder, Colorado when we spoke a few months ago. He is now enjoying the freedom of being able to make spontaneous decisions like this one, as well as taking days off to go skiing, as compared to the more rigid confines of the nine to five.

The decision to go off on his own was sparked when Jay was made redundant and this gave him the extra push he needed to explore the ideas that had long been at the back of his head. Jay speaks honestly about the financial uncertainty and reliance on his savings that have characterised the first few months of his freelancing and entrepreneurial career, given that he hadn’t had the time to build up a new business alongside his job.

Jay also gives some great advice around leveraging your network and knowing when it’s time to shut down your laptop and take a break (or go to bed!).

Watch the full interview or read an abridged version below!

Leaving a corporate job behind to follow your passion: From Escape the City to escaping the country

Jay DikeJay Dike was working at Escape the City, having been in roles including sales as well as housing and construction, when he was made redundant around a year ago – and took this as an opportunity to leave the nine to five. His background had given him a diverse range of experience and expertise including customer services, sales and marketing, and design. Today, he’s running an adventure company where he’s trying to bring people together and guide them on unique trips around the world; he works as a photographer; and he does little projects here and there in various industries.

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

The decision was actually made for me: I was made redundant from my job. I was working with Escape The City – I’m sure many of your viewers will know them. They’re a fantastic company but there were some issues and I was made redundant.

There had always been a little idea in the back of my mind, to have the freedom to go freelance and create my own income. I suppose when I was made redundant it was the fire under my arse to make me do it. I didn’t want to go into another nine-to-five job. I didn’t really want a remote job with one company either; I wanted to try things out and explore my curiosities.

So the decision was made for me, and I’m glad it was! I don’t know how long it would have taken me to actually say, “Let’s quit and try something myself!” Having said that, I would have liked to have the option to keep a full-time job and start something on the side, and make that transition more slowly – rather than cutting it off and starting immediately.

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

Jay Dike travelling
Jay is definitely making the most of his freedom to travel the world as and when he wants…

Probably uncertainty. I’ve been battling with uncertainty and not really knowing where the next paycheck is going to come from, where the next gig is going to come from. In all honesty, and I don’t know how many people talk about this, but financially it has been a huge struggle. Throughout having a full-time job, I’ve always had my savings – which I never touched, they’ve just always been there. It’s the other way around at the moment: I’m living on my savings and whatever I’m earning has just gone to try to replenish what I’m spending. I suppose I’ve only got myself to blame, spending my money travelling!

So those would be the two biggest things: the uncertainty, and the financial side. I’m trying to keep on top of it all – expense tracking and income tracking, budgeting, that kind of thing. I’ve never done that before, so learning how to do all that has certainly been a new experience.

I also feel like an imposter sometimes. You may have to deal with some sort of project or piece of work that you don’t really know a lot about – but you don’t want to say that and you just need to figure it out for yourself!

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

I suppose I was quite lucky with that since, coming from Escape the City, I was surrounded by like-minded and very open, caring people. They have knowledge of the freelancing world and experience in dealing with all the common blockers and struggles that freelancers deal with. Over the eight months to a year that I worked with them, I made some really good friends. They supported me a lot and they were quite active in helping me figure out what it was that I wanted to do next, and how to get there as well. When it came to finding clients, there’s specifically one friend, Johnny, who helped me a lot.

In terms of emotional support, that was a mixture of three of my very good friends who are all entrepreneurs themselves. They’ve each started companies, and failed companies, so I was very much a newbie and they were the ‘big dogs’ who knew all about this world. They were very supportive and were there for me to lean on.

Other than that: Google, YouTube, and just figuring stuff out! I spent hours on my laptop just reading and writing.

I also started meditating, and that really helps to keep your mind clear. I went on a ten-day silent retreat – I could talk about that for an hour! – and it really helped to channel my mental energy and focus on the things that I wanted to achieve.

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

Jay Dike photographer
What a picture!

It’s probably in having the freedom to be where I want to be, and go where I want to go. I’m in Boulder, Colorado, at the moment and I didn’t expect to be here – it was literally a four-day decision. A friend of mine was coming here and I had just become homeless, so it was either do the cliché thing and go to Bali… or come out to Boulder! I had that freedom: I didn’t have to tell my boss that I wanted to go to Boulder, and I didn’t have to see if I had any leave available. I just packed my one bag and came out here.

Also on the freedom side of things, it’s not having to do the nine to five, Monday to Friday. For instance, tomorrow, I’m going skiing the entire day. Whilst I’ll probably be thinking about all the work I’ve got to do while skiing, I can still do it! I can come back in the evening and get some work done then.

A very close second to the freedom aspect would be the connections and the friendships, all the relationships that I’ve formed with people. I have never met and conversed with so many smart and interesting people in such a short space of time. As freelancers, we all need each other to lean on, to find clients, to find advice, and to find solutions to problems. It creates this community both online and offline, and I really love that aspect of it.

My short-term goal is to do the whole ‘van life’ thing. It helps to not have to pay rent! I do want to see a lot more of the world, travel a lot more. At the same time, I also like the concept of having a base for when I just want to switch off from travelling and not showering for four days! To be able to just go home, to my own bed, and have my own stuff. So I’m looking for a balance between those two things, I suppose.

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

I would probably say to really rely on your connections and your ability to be open and gregarious with people. The whole freelancing world, finding clients and being successful, is all about those connections and those networks that you have. You want to be open and giving but also let yourself do some taking every now and then! It’s a reciprocal thing, you ‘pass it forward’. So, all those connections in the past that you’ve made, maybe you haven’t spoken to them in a few years – open those up again, see who’s out there, who needs help and who can help you.

Also, get on top of your finances – don’t let it slip before you realise, “oh, shit, I’ve got no money!” Start doing that now, that’s one of the most important things. And always put money aside for tax – don’t let that catch you up.

Another piece of advice is to set a time in the evening to close your laptop. It’s quite often that I end up working – and I’m not an evening person – until 10pm, 11pm, 12am, and the next thing you know I’m a bit spaced out and the next morning, I’m slower. I think it’s important just to be able to really switch off sometimes.

There’s an overwhelming sense of stuff to do – I suppose we always have these big projects that we want to achieve and we set a certain amount of stuff we want to do in one day. Then there’s always admin, and all those little things – the articles you want to read, a photo you want to post to Instagram, researching what new camera you want to buy… or whatever it might be. You end up falling into a rabbit hole. It’s about knowing when to say: “this can be done tomorrow” or “this can be done within the month”. It doesn’t have to be done right now!

There’s a great quote by Ernest Hemingway around always finishing your sentence half written, so that when you wake up the next day, you immediately fall back into that zone:

“The best way is always to stop when you are going good and when you know what will happen next. If you do that every day when you are writing a novel you will never be stuck. That is the most valuable thing I can tell you so try to remember it.”

I think it’s the same with any task – finish halfway through something, so that you know where to start next time!

You can find Jay on Instagram and on his photography website. You can also find his adventure company at Adventure Goat.

 

Fearless Fridays: Running off to join the circus

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Fearless Fridays with Jo SymoAfter a bit of a break over Christmas, we’re back with Fearless Fridays – and we’re back with a bang! Jo Symo left her job and ran off to join the circus. No, really. She actually joined the circus.

Now that sounds a bit flippant and maybe a bit mad, but the truth is that Jo has been really quite sensible in executing her career transition. She started by taking a few trips here and there, gradually going on more and more adventures, until she had caught the travel bug to the point that she quit her job to join the circus in Australia.

The circus experience showed Jo how many possibilities there were out there in the world, and after another brief stint in the UK working in a leadership and development role she headed off again, this time for 14 months. She volunteered at a camp for people with disabilities in Colorado, travelled from Alaska right down to Panama, and then headed back to that camp having had some an amazing experience the first time round.

When I spoke to her, Jo was back at home doing a five-month contract. This is enough to clear her debts and to pay for the next adventure. As this post goes live, she’s just arrived in Norway as part of an all-female expedition to cross the Finnmark Plateau. Next month, she’s heading back to the circus for a couple of months, and then she has another three-month contract lined up.

I can’t possibly capture our whole chat and all the things that Jo’s been up to in the write-up, so please do watch the full video interview!

 

Leaving a corporate job to follow your passion: Running off to join the circus

Jo Symo

Jo Symo is a leadership expert in the corporate world who helps all levels of managers lead their people to greater success. For a while, when she was tiring of her work, she started going on adventures, travelling… and then joined the circus in Australia! She was the one in the top hat out in front of the tent, bringing people in to see the show. Since then, she has continued to alternate travel and circus antics on the one hand with contract work back in the UK to pay for those adventures.

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

Well, I think I made a pretty massive change when I left an abusive relationship seven years ago, and I just got my head down, and was rebuilding a life, really. Then, I settled down and I got on a flat, and I kitted it all out again. I made this little home, and then I was going away for lots of weekends. Then, I went to Canada for a while. All the while, it was building in me that I just didn’t want to sit still anymore. I’d been sitting still for long enough.

A couple of things happened at work. My team was made redundant, which meant that I left that business. I got some money coming in, and it all seemed to be pointing in the right direction. It felt like it was time to go and see a bit more of the world, really.

On my last day, my colleagues put up pictures of big tops, and circuses, and people were asking:

“Where’s Jo going?”

“Well, she’s going to join the circus.”

“No, really. Where’s she going? What’s she going to do?”

“Yes, really! She’s going to join the circus.”

I find people are split into two camps, really. Either they’ll say, “Wow, I would love to go and do that!” Or others will ask, “What are you wasting your life doing that for?” Quite frankly, I just ignore those people.

It’s my life. I’ve no responsibilities. I have no children. Why can’t I do what I want to do? I’m not bothering anybody. So I’m ignoring the naysayers, and just going and hanging out with people who want to come and do crazy stuff with me, or just want to hear my stories.

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

I think it was deciding where to go and what to do. I’m still coming back doing these contracts, and I’m working hard, so I want the money I’m making here to go as far as I can, and to see as much as I want to.

Another big challenge is being able to catch up with friends and family. I don’t feel like I’m spending enough time with people, because when I’m in the UK, I’m just trying to see everybody. So the biggest challenge is probably trying to juggle the adventures, friends and family, and work.

I’ve been very lucky on the money side. My CV is strong, and people contact me about work. I’m not chasing work, which I think is very fortunate, and maybe a bit unusual.

But they keep wanting me to go permanent, and that just fills me with dread. I’ve agreed to three months, and then we’re going to have to talk, because I planned a bit of a European road trip I want to disappear on. It does feel odd to turn work down. There’s that part of me that’s thinks, “Someone’s offering me work. Maybe I should just go and get another flat…” – but no!

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

I’ve just got the most amazing friends and family, who have stopped rolling their eyes when I say I’m going to do something. One of my friends, who I cancelled on the other day when I forgot I had a mud run on, just responded, “Of course you have! We’ll do it another day.”

I’m incredibly lucky that I have an amazing family who always have a room for me, where I do contribute but it’s the price of having my own place anymore. So, I don’t have to worry about that so much. I live with my aunt and my uncle, and when I came up with the idea of walking across Central America, my aunt just said, “Sounds great. Go and do it. Just be safe.”

I also have my brother, who totally supports what I do, but just wants me to do a bit more work for his business!

I have other friends who live vicariously through me, so will be egging me on to go and do stuff. Then, the more you do… I feel like I’ve got friends all over the world now. So the more I go out and do, and see, and talk to people, the more people I have in different places.

So, I’m really, really lucky that I have all of these people around me saying, “Go for it!”

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

Jo Symo travellingI like the flexibility. I like the fact that when people say, “Do you fancy this?” or when I see something on Facebook, I can just say, “Well, actually, do the dates work?” That’s really what I’m looking at, rather than when I used to sit there thinking, “Oh, I’ve got to pay the rent. I’ve got the bills coming in…”

Also, the amazing people that I get to meet all around the world, who are happy to chat to this crazy English girl, and make me feel really welcome.

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

Just do it.

You can sit there and work out the sums, and work out what you owe, and what you don’t owe; and what you’ve got to earn, and what you don’t; and it’s all irrelevant. My mum always said to me that you can never afford what you want to do. When people say, “I can’t afford to have a child,” she’d respond, “Well, when can you, unless you win the lottery?”

“Oh, I can’t afford to do this…”

Well, when can you?

Life is really, really short. I would rather regret the things that I did do than the things that I didn’t. So far, I’m not regretting them.

So just go for it. Give it a go. What’s the worst that could happen? You end up where you were – but at least you’ve had fun trying.

 

You can find out about Jo’s new project ‘My Great Escape’, aimed at getting survivors of domestic abuse out into the great outdoors for healing, adventure, and a bit of a challenge chucked in as well, on Facebook and on the website. Follow her other adventures on her own Facebook page.