The ups and downs of optimism, when you’re an entrepreneur

Reacting to the outcome of the recent general election, the UK government’s small business expert, Emma Jones (who is also the founder of the UK wide SME-representative organisation, Enterprise Nation), called for entrepreneurs to carry on doing what entrepreneurs are well known for: to face the future with optimism.

It got me thinking about the importance of optimism for anyone starting or running a small business today.

We’ve had a lot to deal with in the last 12 months: Brexit, Trump, the wholly uncertain political leadership of our country, cyber attacks, significant legal and regulatory changes affecting how we work, what we pay in tax or to workers, how we handle data…

And that’s all on top of the daily and ongoing challenges of being in business for yourself. These are often the toughest challenges of all: selling, marketing, designing and innovating, believing in ourselves, even when it feels like others might not; laying savings on the line, eschewing ‘safer’ ways to earn money…all in a bid to make what we dream of happen; asking and persuading others to partner us in sharing those risks.

Emma Jones’ clear statement envisages that as small business owners and founders, we consistently face the future with optimism and that this is vital in these uncertain and challenging times.

But do we in fact face the future with optimism?

And if so, how do we?

In the face of all those challenges us, how we do we keep optimism as a driving characteristic and a defining mindset?

The importance of optimism for entrepreneurs and small businesses

‘It’s very important to be an optimist if you want to run your own business,’ one of my favourite role models and sounding boards, Esther Stanhope, told me. ‘If you were a pessimist, you’d talk yourself out of it in 5 minutes!’

Esther left a great job at the BBC to start her own business. She’s a working mum, juggling childcare and parental ambitions and anxieties around being her own boss. Trusted by some of the UK’s largest and most influential banks, accountants, law firms and numerous small businesses, these days, she makes it look easy. I know it hasn’t been, because her great candour and willingness to share her own experiences and help others not to make the obvious mistakes, have made a huge difference to my mindset and to those of so many others.

She gets the risk that we all find ourselves contemplating, if not obsessing about: the hopes, the fears, the necessary moments of craziness, the sheer need to power through and to believe in yourself.

‘Setting up a business is a huge risk… there are so many what ifs: what if I don’t get clients? What if my overheads are more than my revenue stream? What if I can’t pay my tax bill? What if people think I’m rubbish on stage at the conference?…’

She breaks into her infectious smile and leans in earnestly: ‘Come on, you’ll find the solution’, she counsels confidently. ‘Have faith in yourself. Keep going. Don’t be a chicken…!’

“A rational person would never start a startup knowing the odds of success”

Dazzle’s co-founder and serial entrepreneur, Charlie Cadbury laughs wryly when I ask him about optimism and being an entrepreneur. ‘It’s important for a founder to be unrealistically optimistic at times’, he points out. ‘A rational person would never start a startup knowing the odds of success’, he adds.

The much in demand freelancer and marketing expert, Kim Arnold agrees that optimism is an essential factor in a founder’s ability to get a business off the ground.

‘Optimism is the magic potion that helps you overcome both fear of failure and worries over risk-taking,’ she reflects thoughtfully. ‘It’s critical to running a small business, especially as a solopreneur. This is because unlike with an employed position, you don’t have an annual appraisal or a pay rise to let you know when you’re doing a good job. That has to come from within (or at least until the money’s coming in).’

‘That’s so true!’, Tanya Semerad declares. Newly arrived in the UK from Australia, and impressively multi-talented, Tanya’s busy re-establishing and channelling her performance coaching expertise into a new business (look out for this, even after only a brief sneak preview, I can tell you it’s going to be amazing).

“You have to be able to pull yourself up and keep going”

‘Being a solopreneur, I have only myself to rely on, so being optimistic has been vital,’ Tanya comments. ‘If I’m not optimistic, no-one else in my business is! You have to be able to pull yourself up and keep going.’

According to the serially successful entrepreneur, Adam Elgar, ‘optimism and entrepreneurship go hand-in-hand and there will be a strong self-selecting bias.’

I always enjoy finding out Adam’s perspective on things that trouble or interest me, especially since I’m very newly on my own independent startup journey, eager to learn well from those who have trodden the path successfully before me.

Adam is currently the co-founder of the hugely popular content marketing and blogging solution, Passle. (If you blog and you’re not already using their technology, I highly recommend it.) Passle is Adam’s third startup. Like the previous ventures that he also embarked on with his brother, Tom, it’s been a big success.  But all that success hasn’t come easy and there’s been a lot of hardwork and soul-searching to reach it on each occasion.

‘Optimism is a really interesting subject because it lies at the heart of every project for change, both socially and in business’, Adam shared with me. ‘Whatever we do in life, we all hope that by campaigning, voting and yes, even founding a business, we will be able to influence the world in a positive way.’

“Optimism lies at the heart of every project for change, both socially and in business”

Former Olympic athlete-turned-edupreneur, Josie Horton, also picks up on the theme of influencing others:

‘I believe optimism generates through to others and has an infectious effect. Without it, I would never have started a business or carried on after the accident.’

Josie’s ‘accident’ was no small event in her life. In February of last year, she lost one of her legs in a horrible, freak accident. It was to turn her judo coaching business upside down. But in record time, she was back in business, physically fit and mentally stronger than ever, still demonstrating her expert judo techniques and unbreakable Olympian spirit.

As one of the strongest and most optimistic people I know, she was one of the first people I turned to when researching this blog. (You can find my incredible experience of interviewing her all about her own inspiring and heart-warming personal journey last summer here.)

According to Laura Entis, writing for, ‘irrational’ optimism is, as feels intuitively right, a classic and necessary trait for entrepreneurs. In fact, according to a research study referenced in this particular article, serial entrepreneurs have it stronger than most – even the prospect of failure appears to leave them more optimistic than ever (no doubt because they’ve already proved to themselves that they can hit a great run). And according to Entis, it can very much be a learned trait. She includes plenty of tips in her article, many of which cross over with those contained here.

“Optimism is infectious”

Can you have too much optimism?

Personally, I think you can never have too much optimism. I agree with Josie that optimism is infectious. It’s often a trait of energetic and creative people who have that rich skill of inspiring and motivating others.

Where it’s most powerful, in my experience, is where it’s shown by those who have analytical minds, who can adeptly weigh pros and cons. When people with these personalities show optimism, they can often rapidly convince even the sceptics to have confidence in what is proposed or presented.


and this is a biggie…

“Blind optimism doesn’t make for good business”

Optimism must be well-placed and it shouldn’t be confused with overconfidence or arrogance. You still need to be realistic about your future and what’s involved in making your ambitions real and robust.

Optimism in fact comes from having done your homework and being confident about what lies ahead. It means knowing your target customer audience really well – not just when you start out, but constantly, as your business evolves and the market and consumer behaviour also adapt and evolve.

It means understanding how your customers – existing and potential – feel about your product and what makes them buy it over anything else that competes for the share of their wallet. It also means validating this against the costs and effort involved in bringing your proposition to market – the certain rewards needing to outstrip the costs and risks.

If you haven’t got an honest and thorough picture of these impacts and factors, then you’re not optimistic, you’re foolish.

Nesta’s short and very readable 2015 study entitled ‘Entrepreneurship and Optimism: A double-edged sword’ suggests that:

‘Entrepreneurs are more optimistic than the average person… [O]ptimism enhances the likelihood of identifying creative solutions by altering imagination and increasing positive affect; induces over– confidence in the ability to successfully implement these solutions, which enhances the likelihood of entering the market; generates faulty planning that endangers the success of the venture; and during implementation furthers persistence in the face of difficulties, buffers against stress and helps entrepreneurs in building social capital. We thus show that optimism can be characterised as a double–edged sword – with the potential to help or hinder success during the different steps of the entrepreneurial process.’

Channelling years of solid experience in seeing businesses start and succeed, or struggle, Kim sounds a great warning on this theme:

‘You have to balance optimism with a healthy dose of realism’, she advises. ‘This means knowing your market, your client and your proposition. The lucky few innovators can build a new service or product that creates a brand new market. However for the rest of us, we need to make sure that we are offering something that people really want. Blind optimism doesn’t make for good business.’

“Entrepreneurs must learn to balance their inner cheerleader and realist, and it isn’t always a clear cut line down the middle”

Charlie agrees. ‘Optimism is important to motivate and share an inspiring goal, however, over optimistic targets can be hugely demotivating. Teams need to hit their predefined goals and then celebrate them, rather than feel as though they can never hit unattainable targets. So, it’s always important to temper a founder’s wild ambition with targets than can be achieved.’

Jerry Jao, the CEO and co-founder of Retention Science (a leader in retention marketing) claims that ‘[w]hile studies show a strong link between successful entrepreneurs and optimism, having too sunny a disposition can lead to delusions of success.  It can spur people to overestimate the market and their abilities to execute, while being unaware of crucial facts or possible setbacks.

‘Entrepreneurs must learn to balance their inner cheerleader and realist, and it isn’t always a clear cut line down the middle. Some business situations require more optimism than realism, while others call for a different ratio.’

In his 2013 article for Forbes, Jao provides a series of tips for when and how to balance optimism, pessimism and realism in running a business, from allocating company resources to market testing, to sales and marketing to managing employees.

But if you have done your homework well and set yourself (and anyone working with you) realistic targets, then I wholeheartedly agree with Emma Jones that:

‘…if there is any group that can move quickly to respond to rapidly changing conditions, it is the small business base of Britain’.

Aside from doing your homework, how do you keep optimistic?

“Less optimistic people often refer to themselves as ‘realists’ but it could be argued that optimists are just realists in waiting – meaning that they are just working toward the day when their plan comes together”

For me, being optimistic is more than just being prepared and ticking off the sensible checklist to launching and running a robust small business. I believe it’s also a mindset.

Optimists are ‘realists in waiting’

I don’t think you’re necessarily borne optimistic – or borne pessimistic and cannot then learn to master optimism. However, I do like Adam’s take on how much optimism may be in your nature, as opposed to it having been nurtured and learned:

‘Obviously we are all a product of our environment, but I’m not sure optimism is a learned skill’, he confides. ‘It seems to me that some people are simply more optimistic in the face of any circumstances, while others are perpetually down-beat, irrespective of how well things are going.

‘Less optimistic people often refer to themselves as ‘realists’ but it could be argued that optimists are just realists in waiting – meaning that they are just working toward the day when their plan comes together.’

I used to work with a boss who was consistently pessimistic about almost everything and who never seemed to believe in his own team.

I worked with yet another who believed that if you told people how good they were, they ‘got ideas’ and would leave to pursue new career opportunities. By keeping good people in a state of mental paralysis about their abilities and uncertainty about their value-add to the business, he believed he’d retain great talent and avoid having to pay a higher wage for it.

In both cases, it was a draining and unrewarding experience to work for these bosses, not least since it makes it even harder for individuals and teams to believe in themselves and their ideas.

It’s a challenge faced by many intrapreneurs (those who strive to bring about change from within an organisation, rather than to set up on their own). And in many cases, it back-fires on those very bosses, because if workers are unhappy, they will vote with their feet eventually, even if some take longer to do so than others.

Moreover, people in those teams will never produce their best work or achieve their full potential, to the benefit of those bosses. Brilliant ideas may never be scoped and shared.

But for those individuals who, like me and many others, unapologetically refuse to stop dreaming and believing and who school themselves to be a realist in waiting, the rewards of being optimistic can almost not be overstated.

So I agree that your environment can hugely influence you, but I firmly believe that you can also refuse to allow it to do so.

Keep in mind the advice and tips shared below, they will help you to ensure that you strike the right balance and can achieve the right outcomes even in spite of those whose actions or attitudes may bring you down.

“For those who school themselves to be ‘a realist in waiting’, the rewards of being optimistic can almost not be overstated”

Being mindful and aware – of others as well as yourself 

As I shared above, I believe that those around you and with whom you choose to spend your time, share your ideas and ask for advice, have a lot of bearing on your ability to be optimistic and to feel driven towards launching your goals.

It’s a belief that many of my friends share. Surround yourself with the right people. They’re a key counterbalance to pessimism and negativity, as well as helping to inject that all-important realism.

‘We all get moments of self-doubt’, Kim points out. ‘In those instances, I always turn to my business coach, who reminds me that it’s normal, just a phase and encourages me to look at the general trajectory of my business, rather than the blip that I might be focusing on.’

‘Having a great support network, a business coach and great people around me who understand and help me, keeps me optimistic’, Esther says. ‘I couldn’t run my business on my own. I like having people to bounce off.  Having great relationships with my clients keeps me optimistic too.’

“Self-awareness is the first step to success”

Tanya describes herself as ‘naturally optimistic’. But it’s not necessarily a default.

‘Optimism doesn’t always come naturally!’, she declares. ‘Sometimes, I have to work on it and in those moments when doubt (or a seemingly endless string of perceived misfortune) strikes, I have my ‘go-tos’ that help me to see the silver lining, or better, to understand why my thinking was rubbish in the first place.

‘My go-tos include a quiet place to relax and reflect, as well as podcasts, books and videos by Brendon Burchard and the late Wayne Dyer. I also keep optimistic with awareness. Awareness of my mental chatter, awareness of the news I choose to (or not to) watch, awareness of how I look after my body, awareness of those I surround myself with and more.

‘I’ve learned that self-awareness is the first step to success and therefore I take the time out to be alone, mentally set my path and get myself excited again by remembering how amazing it is to help others and to realise my own goals.’

Josie reflects carefully on this before sharing that ‘being alive keeps me optimistic. I believe I am a realist with moments of pessimism, usually set off by failures and inadequacies, moments of doubting myself and my capabilities,’ she admits.

‘I have learned to turn these around by associating more with positive people; and changing my mindset by channelling my whole being into my strengths and successes, leading me to be more of any optimist.

‘As my business and life grew, so did my optimism. This was a great help to me after the accident. Carrying on my business after it happened, having to focus, gave me an aim and purpose. The constant contact gave me the belief that I could do it.’

Give yourself permission to believe in yourself …and pay attention to good feedback

Sometimes we forget to celebrate. And we overlook or only skim over the good things that people say. A bit of ego is healthy for entrepreneurs. Keeping that ego fed and happy is important.

“Focus on the good. Learn from the bad and move on…”

‘Sometimes I read my emails after an event that I’ve spoken at’, Esther replies when I ask her about what other things keep her optimistic, and how she knows that she is building great relationships with her clients. ‘The great things people say abut my impact sessions really matters to me.

‘The other day I spoke about personal branding at a conference in Brighton and I asked the 200-strong crowd of chief audit executives to create their own personal #hashtags. They all emailed me with their ideas and their feedback. It was hilarious and they told me they loved the session. That’s the sort of reaction that sets my optimism at an all-time high.’

“A bit of ego is healthy for entrepreneurs. Keeping that ego fed and happy is important”

And what about the less complimentary feedback (deserved or otherwise) that we should all expect to encounter, even despite our best efforts to never cause it?

‘Focus on the good,’ Esther firmly advises. ‘Learn from the bad – of course – and then move on. As they say in Silicon Valley: be prepared to fail; and when you do, fail fast, learn and move on.’

Dealing with self-doubt was something that I explored with a number of my entrepreneurial community last summer. You can find my interview containing their great tips on how to handle self-doubt and keep believing here.

Plan ahead, be sensible about your financials and business plan, reach out when you need support

Esther advises that you have plans A-D, and that you never place all your eggs in one basket.

‘Have ‘safety nets’, she counsels. ‘If you have ‘what ifs’ – and you will when you run a business – have strategies for each one.’

‘Earlier on this year, one of my regular clients ‘changed their plans’ and didn’t book me for their usual impact Masterclasses. (I have got more expensive….). In the past, this would have been a real blow to my business and my confidence.

‘But because I’ve learned to plan ahead and to not put all my eggs in one basket, I wasn’t damaged at all. In fact, it left room for better clients to fill in the gaps. Wow! I felt very powerful, optimistic and all grown up!

‘A couple of years ago, without the help, support and advice from my business coach, I would have literally lost the will to go on.’

“The startup journey is an emotional one”

Whether or not as individuals we are demonstrably ‘emotional’ people, the startup journey is an emotional one. It’s important to reach out when you need the extra boost to your self-belief or your own knowledge bank.

Like many of my friends, Josie also recommends this. ‘Staying in touch with parents, colleagues and pupils, reading their supportive and encouraging feedback, focusing on all the positives’, helped her to find the strength and determination to keep going with her highly physically challenging business, even in the absence of both natural legs.

In the very early stages of my own startup journey, someone on whom I’d been depending to help start the business unexpectedly pulled out at the last minute. It was a horrible experience. I didn’t know how to do what this person could do and I had no idea how to find and convince someone to replace him. It caused me to doubt everything that I thought would be possible. I definitely thought about abandoning my ambition.

Looking back, I know now that my reaction was an emotional and irrational one, borne of nerves and self-doubt. I was embarrassed to tell people what had happened, worrying that they would consider me naïve or incompetent, or an unworthy leader.

Reaching into my own network, however, proved to me in no time at all, that as an entrepreneur, you should come to expect these kinds of setback, and that if you ask for help, you will find the right solutions and others will be happy to help you to get there. In my case, those solutions and my brilliant peers (who never once laughed or belittled me), landed me in an even stronger position than I ever would have been.

Are you naturally optimistic? Where does your optimism come from?

‘I’m a happy optimist’, Esther confesses, unapologetically. ‘I’ve always been an optimistic person and sometimes too enthusiastic for my own good. But it’s served me well. I would never have left the BBC and set up The Impact Guru without it.

‘I’m not sure where it’s come from. My lovely husband says: “pessimists spend their life being pleasantly surprised, where optimists are in danger of spending their life being mildly disappointed!” Speaking as a happy optimist, I don’t agree (of course)!’

Tanya recommends identifying ‘go-tos’. These influence her optimism and keep it strong.

‘I’m naturally optimistic’, she states. But that doesn’t mean that she is always on a high. ‘When you’re feeling low, you’ve got to go! Go, where? To a quiet place with closed eyes, a gentleness with yourself and an open mind to what you’re grateful for and the wonderful things coming your way’, she says.

‘Sometimes, my mental chatter is too loud, so I start by listening to music (having a boogie and laughing at myself!) or reading a book with a lovely cup of tea. Books have thoroughly empowered me along my business/life journey and I wrote about this here’.

Mindfulness is something Josie picks up on too. ‘Read the book: The Power of Now’ she recommends, at the same time as encouraging anyone feeling a bit low to ‘phone a friend, reflect on how far you’ve come and what you’ve achieved.’

“Don’t allow your immediate worries to cloud the full picture”

Adam comments that when he thinks about optimism, the film Life is Beautiful (La Vita e Bella) comes to mind. ‘A film which apparently was inspired by the book In the End, I beat Hitler, which,’ says Adam, ‘speaks volumes about the importance of optimism’!

As far as business coaches go, both Esther and Kim recommend Kim Duke at I’d also recommend David Mellor and

And if you’re interested in expert tips on how to plan and review your business, this blog series is a very helpful read, consolidating advice and experience from a number of startup experts.)

Role models

“Entrepreneurs possess the ultimate triptych of super powers: optimism, force of will and sheer graft”

Kim told me that her mother had significantly influenced her levels of optimism.

‘My mother is a huge optimist and has had an amazing range of careers in her lifetime – from cabin crew to sheep farmer, travel guide to estate agent!

‘Her optimism is always coupled with huge drive and an amazing work ethic, which meant she was always successful at whatever she turned her hand to. Failure simply wasn’t an option. Optimism, force of will and sheer graft – I learned so much from this triptych of superpowers. It’s a highly efficient combination!’

According to a poll by Disney Aim High, the results of which were reported in the UK’s Daily Mail in 2014, Kim’s not alone. In fact, in Disney’s poll, parents beat famous entrepreneurs, naturalists and Olympians to be named the nation’s greatest role models.

The Daily Mail reported that ‘more Britons polled named their parents as their inspiration, than notable names including Sir Richard Branson, Nelson Mandela and Mo Farah.’

Josie’s role models are the doctors and nurses who saved her life and pieced her back together. And then there’s her childhood friend, Kate Howey, double Olympian medallist and GB coach, who, she muses, ‘has always been the most optimistic person I know, succeeding far beyond normal physical abilities…’

I confess to having had a number of role models during my 20+ year career. Earlier in my life, a number of those role models were men: from my father, who taught my sister and I that we could be anything that we set our minds to; to my first real boss, who spotted that I was terrified of an initiative that he’d assigned to me and (rather fiercely) taught me to turn off the little voice in my head telling me that I wasn’t ready and couldn’t do it, because he believed and he knew better (he was right!); to another boss, the then CEO of De Beers, Gareth Penny, who is still the humblest, most people-driven and positive person I have ever met.

Later in life, those role models have become a far more balanced mix – to the point where I sometimes feel like I meet a new female role model almost every day – especially in the entrepreneur community.

And male or female, this particular community of like-minded, determined, candid and supporting individuals is intensely empowering. Their optimism seriously does spark ambition and hope in others around them. And it’s not just the emotions that they trigger, it’s the willingness to support others that comes with it, that helps us all to make more new and great things happen.

Long may that continue.

Long may the future that Emma Jones speaks of and that all of us together face, continue to empower us to work together to achieve a continuing, thriving small business community, one that really is capable of forming a strong and powerful backbone for our UK economy.

“The optimism of the entrepreneur sparks ambition and hope in others around them. And it’s not just the emotions that they trigger, it’s the willingness to support others that comes with this, that helps us all to make more new and great things happen”













2 thoughts on “The ups and downs of optimism, when you’re an entrepreneur

  1. Another superb most Merlie and I love the way you repeat some of the most important quotes throughout the article.

    I am fascinated by the ‘nature or nurture’ debate and can say that as one of three sisters, I am ever the optimist, one is a bit of both, and one is mostly pessimistic. Why are we all so different when we three are from the same parents? Is it our genes or our life experiences that have moulded our outlook?

    From my observations, my sister’s pessimism is based on the hope that she will be pleasantly surprised when things do turn out well, and fearing the worst can’t be any worse than the reality. However, more often than not things are as she feared so is it all a self-fulfilling prophecy? Being optimistic seems also to be a self-fulfilling prophecy as optimists tend to implement the things that will lead them towards that positive outcome.


    1. It’s funny, isn’t it. I’m much more of an optimist too, with a healthy dose of realism thrown in. I have a need to believe, I guess, coupled with a determination that if I can believe it, then I need to do all I can to make it happen. Thou I definitely believe in rigorous checking and solid planning!

      My sister is pretty similar. Both our parents too, though I’d say I’m a bit less fearless than my sister and my father. My son has optimism and fearlessness to an extreme!

      But it’s not always easy to be an optimist, especially when surrounded by ‘glass half empty’ people – doubly so if they’re your boss. I’ve had several of those. Hugely pessimistic and negative. Not people-believers. Not willing to see vision or take calculated risks. That’s a challenge. Amazing if you overcome and persuade them even in spite of their default negativity and scepticism. But very hard work!

      I’ve often wondered whether leaders like that are purely acting true to their personalities, or whether they’ve had terrible leaders previously and now don’t feel comfortable leading any other way?

      The strongest and best leaders I’ve ever had were optimists. Highly intelligent, not undue risk takers, but people who were positive, exuded an air of can do – and made everyone else around them, regardless of circumstances or stature, feel they could too. I meet people like that in ‘startup world’ all the time these days too. Inspiring, motivating and productivity-generating. 😊


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