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Some blockers to becoming an entrepreneur

And how to survive them

· Entrepreneurship,fear,blockers

I originally posted this article on my blog Wantrepreneur on June 12, 2016

I can’t tell you what an easy exercise it has been to list out all the things that have held me back in my journey to becoming an entrepreneur. There are many, and the fear is great.

The theme of ‘fear’ is omnipresent in this post. If I were to generalise, I would say it is the thing that has held me back the most, and that holds back many budding entrepreneurs. It is an incredibly powerful and influential force, which will control us if we allow it.

However, if you’re determined to succeed at anything in life, a good strategy is to identify the one thing you’re most afraid of, and tackle it head on. When you begin to realise you can do the thing you're most afraid of, it does funny and wonderful things to your mind, and the sky becomes the limit.

The list below details some things that have been blockers for me at one time or another. Almost all of them involve overcoming fear of some kind, whether it be social, financial, insecurity or public humiliation.

I hope that by reading this list, somewhere out there a budding entrepreneur or two are thinking ‘I can identify with that – that’s me, I thought I was alone in thinking that’. If that’s you, I’d love to hear from you and read your stories too. Drop me a line at, or @claire_ransom on Twitter.

Entrepreneurial blocker #1: self doubt

Why? I know I’ll fail in some way, at some point. The whole idea of starting a business may not work out and I may have to go crawling back to the corporate world.

How I beat this blocker Whilst part of me knows deep down that I can’t make this a success, an equal and opposite part of me (well, perhaps slightly larger part of me) knows that I can do this. I’m resourceful, I take action, I’m a doer, I ‘get’ people: why does that make me any less capable than anyone else who has ever called themselves an entrepreneur? Nope.

Regardless of the outcome, I’ve also realised that I’m more afraid of what I will think of myself if I don’t try this. I can’t bear the thought of living with regret for not having tried. If it all comes down in flames by Christmas, at least I’ll have had a ball finding out whether I can do this, and will have some valuable new skills and contacts to move on to whatever’s next.

At such an early stage in the process, being an entrepreneur is all about state of mind. Everyone has moments of doubt in all areas of life, but it’s how you react to those doubts that makes the difference between success and failure. I know deep down that I’m just as smart as almost pretty much anyone who’s ever tried to be an entrepreneur, perhaps even smarter than some, with more relevant experience. If they can do it, so can I! I have the skills, I have the determination. I just have to give it the time and energy now to make it work.

Entrepreneurial blocker #2: fear of social media and self-promotion

Those social media sharks are definitely going to get me.

Why? I recognize that social media is a very important part of any business’s marketing strategy these days, and for an aspiring entrepreneur, it’s important to have a social media presence. The problem is, I feel incredibly vulnerable on social media. I’m afraid of what my connections on social media will think of me. It’s stopping me putting myself ‘out there’ in the digital world, either on a personal or business level. LinkedIn is about my limit, and I certainly don’t’ make best use of it. I avoid Facebook like the plague and am deeply suspicious of everyone’s motivations on Twitter. I’m afraid of being judged or


How I beat this blocker Whilst I’m still very wary of social media, I’ve taken some steps to overcome this. I’ve started to optimize my LinkedIn profile (you're welcome to check it out) with some new aspirations, I’ve created a personal website (you’re here!), and I’ve made progress with expanding my network and sharing my ideas on Facebook (OK, for now this has just been sending friend requests to my fellow Startup Tribe members and writing a single heartfelt post to my Facebook network to let them know about my new ventures, but I will get better over time). My next steps are to develop an Instagram and Facebook presence for my business idea. I’ve accepted that social media is just part of the gig of being an entrepreneur: if I want it to work hard for me, I just have to get over my hangups and get on with it.

Entrepreneurial blocker #3: I'm not like Elon Musk

Why? To me, Elon Musk is one of the most inspiring human beings of this generation. He is literally changing the future of human civilisation and forcing us all to question what we had previous concluded impossible – or at least impossible within our lifetimes. I can dream of ideas that change the world but I’m not like him, or Steve Jobs.

How I beat this blocker Seriously, who says I have to be like Elon Musk? Aren’t there millions of other microentrepreneurs all round the world, and haven’t there been, since commerce was invented? Stop being ridiculous and just focus on what you’re doing; who cares what anyone else is doing. Elon is amazing, so am I. We’re different, that is all.

Entrepreneurial blocker #4: I'm not an entrepreneur

Why? I have no track record. I have no proof that what I’m doing will be successful. Until I have revenue from my business, I don’t feel I can call myself an entrepreneur.

How I beat this blocker In the first five weeks of the Startup Tribe, I’ve learnt that being an entrepreneur is far more about mindset than actually generating revenue in the first instance. An entrepreneur is someone who ‘takes stuff on’ (to give it the literal French translation). I’ll feel better about calling myself an entrepreneur only once I have a reasonable level of revenue from the business I am creating, but in the meantime, I’m well on the way to getting there in terms of the way I think and act. The important thing, as with all things worth doing, is not to give up.

Entrepreneurial blocker #5: I'm afraid of what my friends will think

Why? I’m so afraid of what my friends will think. My business idea is quite bonkers, even by my own admission. I’m afraid my friends will make fun of me (which they should; that’s what friends are for), but I’m afraid they’ll lose respect for me. So many of my friends are hugely successful in whatever field they’ve chosen; they’re professional, smart and ambitious people. I can’t help but compare myself to them. They’re working their way to the top of whatever organization they’re part of, and here’s me, playing around with a ridiculous idea that may succeed but may also fail spectacularly, and once I’ve told people about the plan, that failure would be very public.

How I beat this blocker My business idea is quite 'out there'. However, over the past few weeks, I’ve gradually started to tell more and more people about it. Their reactions are largely in two categories: they totally get it or they totally don’t get it. Not a single one of my friends has been unsupportive; quite the opposite. They’ve been an incredible support network and source of inspiration and motivation, and yes, they’ve laughed along with me when they learn about the idea, but they quickly come round to it and are intrigued and want to know more. This should teach me to have more faith in my friends. They’re my friends for a reason.

Entrepreneurial blocker #6: I'm afraid of how my family will react

Why? I’m afraid of what my family will think. Primarily, I’m afraid my parents will be concerned for my financial security.

How I beat this blocker Once I had handed in my notice, I carefully sat my parents down (well, by phone) and told them about my plans to leave my job and leap joyfully into the unknown. I told them how important this decision was to me and why I was making it now. They knew how unhappy I was in my current job, and when I had mentioned in the past – quite flippantly – quitting, the reaction was ‘Oh, don’t do that!’.

So I knew my parents would be concerned about the financial side of things. All the same, I talked them through what had led me to that point, and asked them for their support. They gave it freely, of course and said they only wanted me to be happy so would support this decision if that’s what I wanted to do. They wished me luck and asked if they could help. So again, why did I ever doubt them?

Entrepreneurial blocker #7: Financial vulnerability

Everyone wants a place of their own, especially hermit crabs.

Why? I’m afraid I will be risking my long-term financial future on chasing a dream. One of the reasons I stayed in my unhappy job for so long was because my plan was as follows: buy home in London, get mortgage, quit job in London, rent out flat in London, move to Germany (to be with my boyfriend who has been living there since February). However, for boring admin-y-type reasons, I would have had to stay in my job for up to four months longer, if this were to happen, and as I’ve already described in a previous post On abandoning corporate life, I felt my mind was being poisoned by staying there. I simply had to leave, but in doing so, and effectively becoming self-employed/freelance, I immediately cut off the prospect of getting a mortgage and the investment opportunity of owning a property in London. Trust me, I wrestled long and hard with this decision.

Alongside this is the lack of a regular paycheck. Not a small hurdle to overcome, especially living in a city like London, where the cost of living is so high.

How I beat this blocker Over a matter of weeks of thinking about the financials, I began to see (and this sounds like a really obvious thing to say but I did not appreciate the importance of it until now) that not all investments are financial, and that allowing myself time to collect and reflect and develop my interests, although financially painful in the short term, would have longer-term benefits and is potentially the best investment I will ever make. One of the difficulties I’ve had with allowing myself to think this way is that this approach is surely too FUN to be a serious investment! Surely everything that equips me better for life involves some degree of boredom, structure, and following the rules? It turns out I was wrong.

In order to address the day-to-day need for cash in order to support myself, I have developed a plan. Starting from the time I leave my job (late July 2016) until 6 months later (end of January 2017), I will approach my life with a three-pronged attack. This is how long I will give myself to make this new way of life work.

Strand 1 Build a business. I’ll aim to work on this 3 days a week. Get to revenue ASAP. This is my top priority.
Strand 2 Develop a stream of freelance income. I’ll aim to work on this 1-2 days a week. Ideally 1, but up to 2, depending on the work available and timings. This is what Escape the City team refers to as ‘de-risking’ myself.
Strand 3 Write more. I’d love to dedicate a whole day to this every week. This has to be lowest priority in the first six months, as it's the only strand that doesn't have revenue attached to it.

Plan B, should I need it, involves me returning to paid employment early in 2017. I need to do all I can to avoid this and build up a couple of different revenue streams in the meantime.

Entrepreneurial blocker #8: What if it isn't as exciting or as fulfilling as I dream it's going to be?

What does the road ahead hold? Maybe there's a McDonald's round the corner.

Why? I’ve been excited about jobs before. I’ve had jobs that I’ve loved for years, but that don’t change quickly or as often as I need them to. I need variety and don’t want to be working on the same thing for too long, no matter what I’m doing.

How I beat this blocker As with many things in life, JFDI. So plans and people change. So what? I won't know until I try. If I don’t like it, I will make a NEW PLAN! Yes, it's a revolution: I will do something else. And I will succeed. I’ve managed this before, I’ll manage it again. We’re so lucky that we live in a time and a place where change like this and freedom like this is possible. We simply have to choose where to focus our energy, and know what excites us. It’s a pretty big world out there, there’s a lot left to explore.

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