The Voluntary Life: 158 Entrepreneurship is Embarrassing And That's OK

6 June 2014

158 Entrepreneurship is Embarrassing And That's OK

A podcast episode about how becoming an entrepreneur can be pretty embarrassing, and how that's ok.

Show Notes

Listen to Episode 158


  1. Wow, this podcast surprised me! Over the course of half a dozen businesses, I never experienced embarrassment! Most of my businesses were in Australia and New Zealand, so maybe there are cultural differences compared to the UK.

    When other people discovered that I had started up a new venture, I was never uncomfortable or embarrassed. Their most common response was enthusiastic support. Often they told me that they wished they could do something similar. Even if they didn't say that, I could often discern in their body language that they longed to break free of their current job and would love to start a business.

    For sure, the "conscious/unconscious incompetence" stages are real. But you can do it incrementally. At any given time, you are competent in 95% of the things that you are doing, but because you are growing the business organically you are incompetent at the 5% of new, unproven things that you are doing.

    While you are "unconsciously incompetent", you can use those skills on an in-house project so that no-one else suffers as you discover which skills you are incompetent at. For example, when a friend and I started a digital typesetting business in the 1980s (when it first became possible to do typesetting on a PC), we would use each new process or skill on our own marketing and administrative materials first, before we used it on a client project.

    Once we discovered our incompetence, we worked to overcome it by providing "freebies" and "extras" to our paying customers. If they ordered five different poster designs, we might provide them with a sixth "concept design" for free. In the sixth one, we would use new skills at which we may or may not yet be competent, but we would also take the opportunity to think outside the box and present "exciting but less safe" concepts that we normally wouldn't deliver to a customer. At worst, the customer got "something for nothing" but didn't get any benefit from it. At best, the customer loved the sixth "concept design" and gave us a contract to develop the idea further (by which time we had developed our competence further too). Never did it lead to embarrassment.

    For a new business, as opposed to an existing business which is growing incrementally, the solution is slightly different. For example, a website designer would probably build some websites for themselves before they go into business. By doing so, they discover their incompetencies. Then, they would build a few websites "for free" for friends, where it doesn't matter if the work is somewhat incompetent (because it's still much more competent than what the unskilled friends would have otherwise done by themselves). Then, with proven skills and a portfolio, it's time to turn it into a paying business.

    Looking at it now, I think the key to avoiding embarrassment is to avoid portraying yourself as competent when you may not be. Then, when you are competent, you can portray yourself as competent without doubt and with full confidence. Your sales prospects will pick up on that genuine confidence, which will help to win the contracts.

    My message to aspiring entrepreneurs is that you will earn a lot of admiration (if you care about that sort of thing), and have a lot of fun. If you can also get enough cashflow to make a success of it, that's the icing on the cake. Otherwise, the worst case is that you go back to a "job", poorer in cash but richer in experience.

    1. Hi Roger,

      I can understand you want to offer suggestions for how people can ease in to entrepreneurship. However, no amount of preparation can insulate one from experiences like being greeted with indifference by your target customers, or having customers outright reject your sales attempts. Such experiences are an inevitable part of entrepreneurship. Perhaps those kinds of experiences are simply never embarrassing for you. I'm surprised though, if you don't see how fear of such things holds back many people who might want to be entrepreneurs. It’s those people I was talking to.

      You suggest ways to “avoid embarrassment”, and I totally agree that it’s a bad plan to pretend to be competent when you are not. However, I would just emphasise that my main point in the podcast is not to try and avoid embarrassment (you can’t control when you will experience emotions anyway), but rather that you can feel embarrassed and nothing bad happens. Its like the saying about courage: courage is not the absence of fear, you still feel fear but simply choose to act despite it.

  2. Hi Jake, thanks for responding. An inevitable consequence of a free market is that some of one's target customers will be uninterested. Therefore, we don't need to feel discomfort when a sales attempt is rejected, just as we don't need to feel discomfort when we reject someone else's sales attempt. Both of these are perfectly normal, routine parts of doing business.

    For those who do experience discomfort in sales situations, acting despite discomfort is probably the most profitable strategy, but there are two workarounds available. The business can attract its new customers through advertising (e.g. in trade publications). That way, new customers come to the business (usually enthusiastically), rather than the business needing to cold-call on them. I realise that approach would not been easy for your very-specialized business. Alternatively, one can outsource dealing with the fear, by hiring someone else to sift through the sales prospects.

  3. Dude this podcast was awesome. I feel this way all the time and it was great to have it 1) so well defined and 2) see someone else speak openly and candidly about it! It's funny because in my life I have always been drawn to these new "shores" even though I always experience overwhelming embarrassment. It's good to know that it's normal and necessary to get the skills you need to keep moving! Thank you!!


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