This is Part 7 of the special series “Discover the Work You Were Born to Do“, by author Nick Williams.

By the end of this article, you will have explored:

  • The 8 greatest obstacles to becoming an Inspired Entrepreneur.

If becoming an inspired entrepreneur is so wonderful and rewarding, how could anything get in your way? Well, there have never been fewer outer obstacles to creating your own business and becoming entrepreneurial than there are today.

Depending on where you live in the world, to become self-employed legally can be as simple as making a telephone call to your tax authority and then getting yourself a good accountant.

Similarly, technology is no longer an obstacle for most people, and you can outsource many of the areas we need support with. With a telephone and a computer we can potentially run a business with a global reach from a humble desk at home!

When it comes to becoming an inspired entrepreneur, the greatest obstacles – and the greatest opportunities – lie within our own minds, within our beliefs, and within the way we present things to ourselves.

Having made the transition from employment to self-employment myself in 1989, and having helped thousands of others to do the same, I have come to a pretty clear understanding of the major obstacles that you are likely to experience in your own journey.

Some of them are so subtle and insidious that you might not realise the extent of the damage they can do to your spirit. By becoming aware of the eight major obstacles that can squash entrepreneurial dreams and aspirations, you will be able to see them coming and learn to avoid or overcome them:

Here are the 8 major obstacles:

  1. You have too few entrepreneurial heroes and heroines that you can aspire to.
  2. You are afraid to be a pioneer in your work or life and afraid to fail.
  3. You don’t believe you can – or should – make money from doing what you love.
  4. You have great ideas, but don’t know how to bring them to fruition.
  5. You feel you have too much invested in your current career to change now.
  6. You’ve received erroneous opinions from people you respect and love.
  7. You’ve only ever been employed and few of your friends are businesses owners.
  8. You’re yet to understand the power of baby steps and incremental growth.

Let’s go through each of these in a little more detail, and I’ll offer you ways to tackle each obstacle.

1. You have too few entrepreneurial heroes and heroines to inspire you.

These days there are popular roles models such as Sir Richard Branson or the late Dame Anita Roddick. However, the image of entrepreneurs that I grew up with was of characters like Gordon Gekko in the film Wall Street (1987), who was greedy, self-serving and uncaring.

As I was raised in the UK, my other experiences of entrepreneurs included characters such as Arthur Daley in the television series Minder and Del Boy in Only Fools and Horses. In essence, they were dodgy, opportunistic but nonetheless likeable rogues. All the same, although I liked the idea of being an entrepreneur, I didn’t want to be like them, and yet I had very few other role models to model myself on.

Question: Do you have many inspiring entrepreneurial role models? Who do you look up to?


  • I bet that within a mile of where you live, there are probably dozens of self-employed people who are doing things they love. Seek them out, spend time with them and ask them questions.
  • Read stories of people like yourself who have followed their hearts and done something successfully.
    Go to meetings where entrepreneurial people congregate.

2. You are afraid to be a pioneer in your work or life, and afraid to fail.

We may start off with an adventurous spirit, hungry to learn, but as we grow up and enter the world of work that spirit often gets dimmed – and increasingly – we tend to stick with what we know.

Our thinking may be along the lines of: ‘I haven’t done it, so I can’t do it’ or ‘I’ll do it, but I want to avoid looking stupid or failing at any cost’. What’s really going on here?

Pride and fear: By definition, if we have never been self-employed and decide to make the transition, we’ll start doing things that we’ve never done before – and that’s precisely what makes it so exciting. We can create our own way in life by moving off conventional and seemingly safe career paths.

The bottom-line question is: do you want to move in the direction of your deepest dreams and desires, or shrink your life by remaining a hostage to your fears?

In order to achieve great things it’s likely you’ll encounter fear, sometimes great fear, but here is what you should know: the bigger the fear, usually the greater the reward and fulfilment you will experience when you conquer it. Feeling fear doesn’t mean your idea is bad or wrong – often quite the opposite. It demonstrates how much you care, how much passion you have, and how big the draw is for you.

This path is not about being neatly organised and eliminating all your risks in advance. You will need to learn to live with and tolerate ambiguity, confusion, paradox and contradiction. At times you might even find yourself in chaos, but out of that chaos your creativity can begin to emerge.


  • Make friends with your fear – recognise it as the pointer that it is and do not use it as a ‘Stop!’ sign.
  • Develop your courage – you already have it within you – so start to draw it forth in small ways by consistently doing new things that break you out of your current limits. Your courage will then become a ready resource for you when you need it.
  • Begin to enjoy the excitement that growth entails – beyond your fears lie great riches. Every fear you overcome is like a skin you shed and you will grow more confident in the process.
  • Keep your focus on the rewards you reap by facing your fears – the freedom, joy, creativity, money, love, appreciation, self-esteem, self-worth and success that await you. Keep reminding yourself that short-term discomfort is a small price to pay for greater rewards.

3. You don’t believe you can – or should – make money doing what you love.

If we have only ever earned our income doing work that we haven’t particularly enjoyed, or that we have actively disliked, we may find it hard to believe that people will willingly and happily pay us to do something we enjoy doing.

Even if we haven’t had a specific religious upbringing, many of us in the West have been influenced by the Protestant belief that we shouldn’t be paid for doing anything that feels good. In fact, we may have been taught that money is the compensation we receive for not having enjoyed our work.

Inspired entrepreneurs don’t believe they have an implicit entitlement to money – they know that money flows to them as a result of the value they add to other people’s lives. So they are motivated to add value in the knowledge that success is the natural reward for their contribution.

They know that money doesn’t flow merely in return for hours worked, but in exchange for great ideas well executed. Inspired entrepreneurs know the power, and value, of great ideas. They don’t think of their business as a single source of income; they think of multiple sources of income.


  • Think of the people whose company you are grateful for and with whom you are happy to spend money – then imagine those people being equally happy to spend money for your own products or services.
  • Start thinking of money as a blessing that you are grateful to receive.

4. You have great ideas but don’t know how to bring them to fruition.

The first question that often follows hot on the heels of a brilliant idea is this: ‘But how on earth could I ever do that?!’

Knowing how to bring your ideas to fruition
The issue of ‘how’ suddenly becomes paramount and many people become instantly discouraged because the means to accomplish their dreams may not immediately be apparent.

However, we don’t need to know exactly how we are going to achieve something; often it is a blessing not to know as it is this that makes the process such an adventure. We can learn as we go, not just before we set out. Don’t get too practical too soon!

We need to have a destination, but even a vague sense of direction will be enough to get our momentum going. Remember: you can clarify your course as you go.

Most people who have achieved anything significant in their lives were not clear about how they would do it when they set out. It became clear as they went along only because they had already started their journey.

You only have to know that it will happen – you can and will learn as you go – the important thing is that you start building momentum. When your love and your skilfulness come together, you will create masterpieces.


  • Research and find out how others have done it. Whatever your idea, many people will have done something similar before you. How did they do it?
  • Ask others if you can – a radio-producer friend of mine wanted to know how to start her own radio station. She took various people she knew out for lunch and asked them how they thought she might do it. She learned so much that she described it as, ‘A PhD over curry!’ She now has her own radio station.
  • Plan the next two or three steps and let the larger plan emerge as you go. Don’t be afraid to cross bridges when you come to them.
  • See yourself as having already achieved your goal, and then ask your future self, ‘How did you achieve it?’ Discover what that future projection of yourself has to teach you in the present moment.

5. You feel you have too much invested in your career to change now.

Many people I’ve coached are on the threshold of positive change when they start worrying, – ‘But I’ve invested so much time and energy in my career so far. I can’t bear to throw that away. What a waste that would be!’

Another variation is: ‘This job is who I am! So much of my self-worth and my sense of identity are tied up in my job title, my status and position. I don’t know who I would be without them. I need them to feel good about myself.’

These are genuine and valid concerns, but they are also obstacles to change. It amazes me that we would sometimes rather waste the rest of our lives than ‘waste’ an education. But the truth is that nothing we have ever done or learned is ever redundant.

Our total experience has brought us to where we are now; it has grown us, shaped us and made us more confident and clearer about our aims – even if being clearer means that we recognise we dislike our present situation and want to move on.

We should be grateful for all our experiences and nevertheless remain willing to move on. And, yes, we may move into a temporary void – and that may be uncomfortable for a while – leaving us wondering who we are. But nature abhors a vacuum and soon a new and greater sense of ourselves will emerge, and we’ll like ourselves a lot more!

The temporary discomfort of growth is well worth the new confidence and identity that will emerge. Discomfort is usually a good sign, an indicator that you are pushing your limits and growing. One simple step that creates success is when we dare to move outside our comfort zone and then stay outside them long enough to grow into a new sense of ourselves – rather than shrinking back to the familiar.


  • Reflect on all the changes you have already been through in your life and how much your sense of identity has changed.
  • Consciously put yourself in places of discomfort in order to grow into a larger sense of yourself.

6. You have been subject to erroneous advice from people you respect and love.

As soon as you start telling family or friends you’re thinking about starting our own business, you may find yourself on the receiving end of a torrent of advice. Some of it may be unhelpful, some discouraging, and some of it may be useful and encouraging…

…but here’s the bottom line: most of this well-intentioned advice will come from people who have never taken this step themselves. So their advice may be based on hearsay or have little grounding in fact and experience.

We may encounter cynics who’ve never had the courage to follow their hearts – but yet they’ll tell us we’re crazy to be considering this move. We may meet disgruntled business owners who’ll tell us to stick with our jobs and be more realistic. When it comes to business, it seems everyone’s a pundit – every cynic who’s picked up a newspaper likes to trot-out statistics about how many small businesses fail.

We need to become discerning about who we listen to. A wonderful piece of advice comes from the mystical poet Jalal ad-Din Rumi (1207–73), who said, “When embarking upon an adventure, do not consult someone who has never left home”. So whenever you are offered advice, bear this mind: consider the source.

This means checking out whether the person in question is a card-carrying Inspired Entrepreneur themselves. If so, listen to them; if not, be very, very discerning, even if they are someone you love, respect and care for. They may simply not know what they are talking about in this area.

It is an uncomfortable fact that many of the people we love, look up to and respect simply don’t know what they are talking about when it comes to being self-employed. Don’t let your fragile dreams be crushed by bad advice.


  • Develop a degree of discernment about the advice you receive – always consider the source and ask yourself: ‘To what extent should I be listening to this person?’
  • Create a list of people you would like to receive advice and guidance from – your mastermind group – and then take steps to start receiving support and guidance from them.

7. You’ve only ever been employed and too few of your friends own businesses.

If you grew up in a household where everybody was an employee, and most of your family and friends worked a 9-5 job, then you may have inherited a lifetime of thinking and acting as an employee – not as an entrepreneur. So it is hardly surprising that many of us have a void in our knowledge about entrepreneurship!

From the outside, entrepreneurship can seem like a parallel world – exciting, mysterious and appealing, and maybe a little scary and unknown too. In the absence of solid knowledge, facts and actual experience, we are likely to fall back on our existing prejudices and opinions, and so becoming an entrepreneur can be like learning a new language.

There are many differences in the ways that employees and entrepreneurs look at the world. One of the biggest differences is that inspired entrepreneurs have a greater willingness to take responsibility for their lives, knowing that both their successes and their failures are down to them.

Successful entrepreneurs don’t look for excuses or anyone to blame, not even themselves. They are willing to be visible, and when things don’t work out they want to learn and adjust their course.


  • Reflect on your own preconceived ideas about being an entrepreneur – exactly how well-founded are those views?
  • Read articles, books, biographies and stories by and about inspired entrepreneurs.

8. You’re yet to understand the power of baby steps and incremental growth.

Every business starts with the first steps and then with the first customer, the second and the third customer. It may take several years before the operation is scaled up to become a substantial business.

Any business is a seed that can blossom – but patience is necessary!

One of the biggest mistakes many people make is to focus on the gap between where they are right now and where they want to be. Sometimes they think it’s so huge – and insurmountable – that they can’t bring themselves to take the first steps.

Another mistake is that they take the first few steps – and then stop – because those tentative baby steps didn’t seem ‘sexy’ or significant, or catapult them directly to fame and fortune. The truth is that every step, however small, moves us forward as every step builds on the step before.

As we have seen, we often only find the confidence to do something when we are actually in the process of doing it. This is why baby steps can give us access to resources that otherwise lie dormant within us. At times we may also experience quantum leaps and breakthroughs, but these will often be as a result of our previous baby steps.

One of the most powerful things we can do is to make the most of what we have right now. The belief that every step on the way must be ‘sexy’ and exciting can be a great obstacle. In contrast, baby steps can throw wide the floodgates of momentum, abundance and magic.

Small deeds done are more potent than great deeds planned, so think big, and keep your mind on your ultimate goals – but act small. You cannot avoid investing energy and labour by taking short cuts to glory. The idea that massive leaps of faith pave the way to success is deceptive, and in fact many leaps of faith are actually achieved through gentle little steps.


  • Regularly ask yourself, ‘What baby steps can I take next?’
  • Take new action on a regular basis in order to start and build your momentum.

Sometimes we block ourselves from acknowledging our innate entrepreneurial spirit – especially if it has been perceived as a problem in our previous roles as employees.

For example, the entrepreneurial spirit is forever questioning why things are done the way they are, thinking about how those things could be done better and making suggestions for change.

In some environments this spirit is welcomed, whereas in others it can be seen as a problem and we are told – ‘Why you can’t you just accept things as they are and do your job?’ So recognise that your own entrepreneurial gifts may be perceived as a problem if you are living and working in non-entrepreneurial environments.

If we follow our entrepreneurial spirit we will also learn to recognise, rely on and trust in unseen forces. Whilst our ego generates resistance, we also have unseen allies and positive forces supporting us. As we take action consistently, we’ll find synchronicities occurring in our lives; for instance, chance meetings, affirmations and opportunities may come our way.

Positive unseen forces are working on our behalf and the Universe itself is designed to support our joy, our creativity and the liberation of our potential. There are no universal forces pitted against us – just our own resistance!

About the Author

Through his books, and live talks, workshops, personal coaching and on-line learning programmes, Nick Williams has inspired tens of thousands of people to discover the work they were born to do.