Kelly Cookson of Cheer Up Marketing On Becoming Free From The Fear Of Failure

An Interview With Savio P. Clemente

Savio P. Clemente
Authority Magazine
Published in
14 min readNov 4, 2022


Become aware that the fear of failure can be overcome by training yourself to become growth mindset oriented instead of fixed mindset oriented. You can change your perception of failure. For example, I reflect on every “failure” and challenge the negative beliefs this experience has created for me. I ask myself if the stories I’m telling myself about this failure are true (spoiler alert: they are NOT true) and then I write down all of the learnings from the experience.

The Fear of Failure is one of the most common restraints that holds people back from pursuing great ideas. Imagine if we could become totally free from the fear of failure. Imagine what we could then manifest and create. In this interview series, we are talking to leaders who can share stories and insights from their experience about “Becoming Free From the Fear of Failure.” As a part of this series, I had the distinct pleasure of interviewing Kelly Cookson.

Kelly is an Email Marketing Mentor & Positive Psychology Coach and the founder of Cheer Up Marketing. (

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

Thanks for inviting me here today!

So I grew up in a very typical working-class family. My parents were both bus drivers, we lived in a 3-bed semi and university wasn’t high on the agenda for myself or my sister. In fact — no one of our family name had ever been to University.

My early years started like that of any other kid from my background, but it wasn’t until my mum made the brave move to change her life that I soon discovered that my future could be different, too.

When I was 8, my parents split up and my mother started to redesign her life — she went back to school to get her A levels, then a degree and eventually got a PhD in Organic Chemistry and started a new career. She’s my absolute hero and the inspiration behind my drive and ambition!

I eventually went to university when I was 23 and went on to graduate with a first-class honours degree in Business Information Management and immediately started my career as a Marketing Manager. I landed a job as a Marketing Assistant at a law firm within a week of submitting my final year project! I learned so much at that time of my life — not just about marketing but also about the kind of work I really wanted to do and I visualised working my way to the top of the corporate ladder to become Marketing Director or CMO one day.

My ambitions drastically changed after the birth of my daughter. When she was 2, I made the leap out of employment to start freelancing and even though some of my colleagues thought I was mad for leaving the security of my job, I knew it was the right thing for me. I craved flexibility and I knew that I could make more money doing my own thing.

Email marketing has always been my jam and I love copywriting, so the natural progression for my new freelance business was to stick to my zone of genius. If it ain’t broke — don’t try and fix it! And for a while that was great for me — I was going it alone, I had lots of clients and my skills were in demand.

But self-employment wasn’t quite how I’d hoped. During those first 6 months, I felt stressed, overworked and still not earning the money I wanted — although I’m proud to say I matched my corporate salary in my first month freelancing; I just knew I was capable of more.

I ended up meeting an intuitive mindset coach and signed up for a few sessions to help me define what I really wanted from my business and how I was going to achieve this. And, oh my word! This was the best decision I ever made! That initial coaching experience set me off on a journey to develop my mindset for success and ultimately led me to discover Positive Psychology. In fact, I’m so convinced by the power of positive psychology for entrepreneurs that I qualified as a coach and have started using positive psychology with my marketing mentoring clients!

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

I first got the entrepreneurial bug about a year after going back to work from maternity leave. I was working part-time and I got a sense that I had a bit of time to build something on the side to make some cash and stretch my creativity. I was a big fan of the Side Hustle School podcast by Chris Guillebeau and felt super inspired by all the weird and wonderful ways people were adding new income streams.

Some side hustles I tried out before I started Cheer Up Marketing:

- Flipping vintage clothes on Depop. My best charity shop find was a Burberry jumper for £4. I sold it for £45. My husband is a minimalist kind of guy and I could tell the piles of second-hand clothes were stressing him out so I re-donated my surplus stock after about 6 months.

- Selling digital art on Etsy. I sold a grand total of zero.

- Pet portraits. OK, I didn’t take this to market after trying to draw my cat and realising no one would pay me for that! This was inspired by an episode of Side Hustle School where a woman was making $6000 a month drawing pets.

In the end, I discovered it was MUCH easier to make money doing the thing I had a degree in and over ten years’ practical experience — marketing.

You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I’m an excellent communicator — I seem to have the knack of being able to explain my ideas and vision to others which enables them to come on the journey with me. I use this skill with my clients, teaching them marketing strategy and in turn, helping them to communicate their vison and expertise to their ideal clients. I also use this communication skill to listen to my clients during our coaching sessions and to add my observations to their reflections, helping them to have a deeper understanding of how their mindset and character traits come into play in their work.

I’m a big fan of the VIA Character Strengths Assessment which is a tool I learned about during my Positive Psychology Coaching training. My top strength is humour! When I first got the results of the assessment, I felt a little disappointed that humour came out on top — after all, what use is humour when trying to build a business empire? It turns out it’s a huge help! I use humour every day with my clients as I love to laugh together and share a moment of lightheartedness. I’ve also recognised that I need laughter and fun to feel motivated and energised at work. This has led me to be proactive in seeking moments of silliness, laughter and fun in both life and work, something I credit with keeping stress at bay and making the ride on this entrepreneurial rollercoaster more enjoyable.

Choosing another characteristic from the VIA Character Strengths — Hope is also in my top 5. Hope for the future manifests for me as feeling excited about the business I’m creating and the results my marketing strategies and coaching bring for my clients. I think you need hope for the future to be a successful leader because at the end of the day, if you aren’t hopeful, how can you expect the people you lead and collaborate with to bring the best of themselves to the task at hand?

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the concept of becoming free from failure. Let’s zoom in a bit. From your experience, why exactly are people so afraid of failure? Why is failure so frightening to us?

Luckily for me, I don’t have a high fear of failure when it comes to running my own business. I am naturally growth-mindset oriented and I remember when I handed in my notice at work to start my own business, I had no doubt that it would work. I accepted that I would need to test out different services, marketing messaging and ways of working to find my sweet spot. I was open to investing in support to develop myself as a business owner and for trying new things.

How did I become relatively free of the fear of failure when it comes to running a business? It comes down to my natural disposition in terms of having a growth mindset.

What do I mean by ‘growth mindset’? And how do you know if you have a growth mindset or if you are more of the opposite — experiencing a Fixed mindset?

A growth mindset focuses on the journey of experiencing, giving things a go, failing and learning until you succeed.

If you have a growth mindset, you likely view life events as opportunities to grow. This is something I proactively work on because I’ve experienced failures in my business and I’ve sat down each time and reflected on why things didn’t work and what I would do differently next time.

When you approach life and business this way, failures are only temporary setbacks and opportunities for improvement and learning. People with a growth mindset take charge of their success and the process of attaining it and keeping it going.

So what about the opposite? What does it mean to have a Fixed Mindset?

When your fixed mindset comes into play, you might see setbacks as hard to overcome, viewing things as permanent and unchangeable.

A person with a fixed mindset sees things as absolute and when things go wrong, they go into victim mode. This is why people often fear failure — it seems as if failure is terminal. This fixed mindset limits your potential as you hold back from trying new things and taking risks. Risk-taking is an unavoidable part of becoming a successful entrepreneur. I also view risk-taking as investing money into your business. I have done this from the outset to upskill myself and outsource tasks that took up my time so I could free up more mental space for creativity. I put some of my early investments on a credit card because I knew I needed that support to grow. I was correct.

In summary, being free from failure for me is about adopting a Growth Mindset wherever possible. A Growth Mindset can be learned and developed — this is so exciting for people who are naturally more Fixed Mindset.

There are numerous studies on Growth Mindset vs Fixed Mindset and I highly recommend the book ‘Mindset: The New Psychology of Success by Carol Dweck.’

What are the downsides of being afraid of failure? How can it limit people?

When you run your own business, being afraid of failure will hold you back from the success you are capable of achieving. It prevents you from taking risks, investing in the support you need to scale and investing in your own personal development. It can hold you back from putting new offers out to market and sharing your vision with the world.

If we don’t address our fear of failure, we will fail. There’s no doubt about that.

And that’s where the cycle begins because if fail then we’re feeding that original fear and once you’ve fed the fear, you’re telling it that it was right. You’re giving your fear of failure more ammunition to use against you!

In contrast, can you help articulate a few ways how becoming free from the free of failure can help improve our lives?

If someone can overcome the fear of failure then, essentially, they can become unstoppable in life and business. Not only will they open up new possibilities they will stop limiting themselves in what they strive for — whether that’s more money, a better relationship, an exhilarating experience or better health.

In theory, the more they do the things that they had previously deemed as a ‘surefire failure’, the easier it will become — potentially opening up their willingness to try even more adventurous pursuits!

We would love to hear your story about your experience dealing with failure. Would you be able to share a story about that with us?

When I look back on my journey so far as a business owner, I truly struggle to recall experiences of failure! Things have gone wrong in terms of mistakes I’ve made and plans that didn’t yield the results I was hoping for but I’m definitely walking my talk here and have applied a growth mindset to every setback I’ve experienced so far.

To share an example of a “failure”, I used to run a low-cost membership where business owners could access my support and expertise by paying a low monthly fee of £30. I saw this as a perfect way for me to help others who couldn’t afford my higher-priced services and a way to make semi-passive income as all I needed to do was show up once a week to answer my members’ questions. I ended up finding it ridiculously hard to sell this £30 offer! Looking back with hindsight, I didn’t have the audience numbers to sell this in a large enough volume to make it pay. I put tonnes of effort into creating the member’s area content and in launching it to make a recurring monthly income of around £200. It wasn’t financially viable and I failed to enroll new members in large enough numbers to make it work, so I ended up closing it down after a few months.

How did you rebound and recover after that? What did you learn from this whole episode? What advice would you give to others based on that story?

What did I learn from this failure? That it was worth testing out a new income stream but it proved to me that my model of higher priced, high-touch services were where the real money and clients results are at. I had to let go of the hours of creative energy I spent putting that membership together and chalk it up to experience,

I stuck with my zone of genius after that.

There’s also some pricing advice I would give to new business owners: don’t be afraid to sell your services at the high price they should command when you look at your years of expertise and the level of service you provide your clients. It can appear easier to sell something for a low price but unless you’ve got money to throw at paid ads to drive traffic (and bags of time to experiment with this) — stick with what you are good at and charge a fee that reflects the service. It isn’t easier to sell something cheap than it is to sell something higher priced.

Fantastic. Here is the main question of our interview. In your opinion, what are 5 steps that everyone can take to become free from the fear of failure”? Please share a story or an example for each.

Step 1 = Become aware that the fear of failure can be overcome by training yourself to become growth mindset oriented instead of fixed mindset oriented. You can change your perception of failure. For example, I reflect on every “failure” and challenge the negative beliefs this experience has created for me. I ask myself if the stories I’m telling myself about this failure are true (spoiler alert: they are NOT true) and then I write down all of the learnings from the experience.

Step 2 = Look for stories of successful people you admire who have overcome failure to get to where they are today. These stories should inspire you and push you to try to become who you want to be.

Step 3 = Visualise success. When I am looking to reach a new goal in business, I visualise it as if it has already happened. I imagine my ideal clients saying “yes” to working with me. I imagine the event I’m running to be full of amazing participants. I plan what to spend my money on once I’ve made it! This visualisation should bring forth feelings of excitement that you can lean into when fear starts to surface.

Step 4 = Share your hopes and dreams with someone. I find one of the best ways to push myself out of my comfort zone and DO the thing I’m feeling afraid of, is to share this dream with my husband, mum, sisters, best friend etc. Speaking it out load means it’s more than just an idea. Others will be glad to support you to reach your goal which helps to make it a little less scary.

Step 5 = I also love to create a “Hope Map” for my projects and goals which also has space to include who I need to get support from to make it happen. Doing it alone is more scary!

The famous Greek philosopher Aristotle once said, “It is possible to fail in many ways…while to succeed is possible only in one way.” Based on your experience, have you found this quote to be true? What do you think Aristotle really meant?

I think to know what success really means, you need to set a goal. In business, this probably looks like financial targets and I do have those goals but I also set goals in terms of how I want my life outside of work to look. For example, I want to spend time with my young daughter and go to the gym instead of being at my desk all the time! In terms of meeting those goals as a success, yes — I can say I’ve either done it, or I haven’t.

In life and business, there are always going to be things that get in the way of success and you probably don’t know what half of them might be! So, yes, I think failure can happen in a variety of ways but applying a growth mindset to them is what makes them learning experiences rather than crushing defeat.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. :-)

To be honest, my ambitions for change and bringing good aren’t as grand as a movement to help millions of people. I find that overwhelming as a concept. Instead, I prefer to look at good causes I can support closer to home such as supporting the local food bank, donating to local charities and giving my time to my daughter’s school where they need adults to help out. I think the ripple effect of doing small things in my local community has the potential to spread wider afield. I think the movement I’d like to inspire is giving a little time to help those around you who need it. Kindness also goes a long way. Having a chat with a stranger or doing random acts of kindness also has the potential for that ripple effect of spreading good feeling.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them :-)

I’d LOVE to sit down with Wim Hof. I do his breathwork most mornings and I’ve recently become a convert to cold showers. I find his whole vibe to be incredibly calming and inspiring at the same time. I’d love to meet him to see how this is amplified in real life! I think I’d leave that meeting feeling ready to take on the world. That’s how I like to build myself up to feel each day through breathwork, visualisation and applying the growth mindset techniques I’ve shared with you here. I’d be walking on air and ready to push through to my next level if I met Wim.

How can our readers further follow your work online?

I’m most active keeping in touch with my email list — you can join at

I also hang out on Instagram @cheerupmarketing

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.



Savio P. Clemente
Authority Magazine

Board Certified Wellness Coach (NBC-HWC), Journalist, Best-selling Author, Podcaster, and Stage 3 Cancer Survivor