Back on the Rollercoaster

by stevew on February 19, 2010

It’s well known that when starting a software business, the idea isn’t the most important thing. As Jason Cohen points out:

Your idea probably sucks, and it doesn’t matter because your business will probably turn out to be something completely different.

When you’re working in a self-funded start-up, though, you feel it must matter, at least just a little bit. The point is: how many second-rate ideas can you afford to burn through until you run out of cash? In the mind of the bootstrapping entrepreneur, this question can generate a paralysing fear all of its own, which goes along the lines of “Do I stand a chance of being successful with this thing I’m working on, or am I’m going to run out of money in the pursuit (and have to go back to the job market with my tail between my legs)?”.

Previously I talked about how to deal with external sources of negativity – this post attempts to provide some thoughts on dealing with the voice from within, as I’ve been facing this very fear during the past week. Hence I thought it would be interesting to talk a little about the more general issue of dealing with self-doubt.

I wondered if this lack of confidence was just me – a genetic personality flaw amplified by my upbringing or my past experiences. However, when I started to do some research, I found that many believe it is part of an entrepreneurs’ standard make-up, as for example Tim Ferriss, author of the The 4-Hour Workweek suggests:

It’s an integral part of building anything remarkable, whether a business, a relationship, or a life. Expanding your sphere of comfort and abilities comes with a cost: repeated self-doubt.

In researching how to deal with this self-doubt, I came across Canadian Business Coach Cameron Herold – he describes a tool he calls the Transition Curve, which is a little reminiscent of the four stages of competence. It looks something like this:

Transition Curve
It isn’t completely clear what the vertical axis means, but the horizontal axis is obviously time – note that this cycle often repeats itself many times over in the life of a start-up. In any case, it’s quite a helpful model on how our feelings tend to operate as we move forward in any new business, past the initial optimistic phase, into the will I ever ship?, will anyone want it?, why are we here? phases and then (hopefully) into the hey, this is actually working! phase.

Whilst I’m not really a proper mathematician (as the following results show), I felt it would be interesting to differentiate the curve, hoping that this might give some better indication of “mood” over time. Here is the result:

Transition Curve, differentiated
(Above the axis is good, below the axis is bad. In the spirit of Uninformed Optimism, I’ve omitted the Crash & Burn option).

The first observation is that when you’re at the points of worst self-doubt, the only way is up, and while you might not feel too good about things, the trend is definitely a positive one. The second observation is that the fundamental shape of the curve is unchanged – life in a start-up is much like being on an emotional rollercoaster. I confess I’m not a big fan of fairground rides.

The question then, is how best to deal with this emotional cycle, especially at the low points where your demon of self-doubt is at his most active? First it helps to know that everyone goes through it at some point, as noted above. Secondly, it’s important to resist the temptation to ‘stall’ – if fear causes you to freeze like a rabbit caught in the headlights, then in the best case, you stop learning through making mistakes, and in the worst case, you fail to reach a perfectly attainable goal. (The tendency to want to give up in the face of adversity is captured nicely by Seth Godin in a guest post on the excellent Zen Habits blog). Thirdly, ask yourself the question “what’s the worst that could possibly happen?” – it probably isn’t half as bad as you first feared. (I picked this tip up from Bob Parsons, founder of GoDaddy, where he quotes his father’s advice: “… if it doesn’t work, they can’t eat you!“).

Practically, this last point was a real help to me this week – I realised that even if I failed to make a business out of the software I was building, I would still have developed substantial expertise in a niche where few people are experts and demand is only set to grow. So my “what’s the worst that can happen” scenario is that I end up leveraging this expertise through high value consulting, while I look for the next big idea.

The key message is that whilst there may be plenty of reasons to revisit what you are striving for in your start-up, fear of failure shouldn’t be one of them!


  1. Cameron Herold describes the Transition Curve in this Canadian Business Online podcast.
  2. The Prescription for Self-Doubt: Watch This Video – short article by Tim Ferriss containing a very moving video about going forward in the face of adversity.
  3. Bob Parsons’ 16 Rules for Success in Business and Life in Generalthey can’t eat you and other motivation tips.
  4. (Relating to the supremacy of ideas) Ed Catmull, founder of Pixar gives an interesting talk about the history of Pixar, where (amongst other things) he makes the point that having great people is more important than having great ideas.

Did this strike a chord with your experience? Perhaps you have other tips for dealing with fear or self-doubt? Please leave a comment and let me know.

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{ 6 comments… read them below or add one }

Mark Dalgarno February 21, 2010 at 9:36 am

Very useful Steve.

I’ve certainly stalled a few times but find a few things help:

- Like you, a realisation that I’ve acquired lots of unique, valuable experience along the way
- Reflecting on the huge amounts of good things we have actually achieved in the short life of our company
- Drawing on a large support network that we’ve built both locally and internationally
- Realising others are in the same boat
- Not being afraid that we might fail, as you say – what’s the worst that can happen?
- Celebrating successes, no matter how small
- Learning from failures – being better prepared to address future challenges.
- Realising that the longer we’re around in business the longer we’re likely to be around in future



stevew February 21, 2010 at 9:57 pm

Thanks for the feedback Mark. I think the last point is particularly interesting – assuming you’re not in imminent danger of running out of cash, for each day that passes, your odds of long-term survival climb, non-linearly I would argue. It would be very interesting to do a study on that subject – people argue that survivor bias can be misleading, but perhaps this is one area where it works to your advantage…


Rui Curado February 21, 2010 at 10:15 am

This is a quite revealing post and I can say I’ve been riding the rollercoaster for some time. Especially if your startup involves the creation of new concepts. If you look at my startup at, you’ll find three projects that are actually concepts in their very essence.

This brings an additional doubt to your equation which is the fear of others not adopting your concept:

- Will they like it?
- Will they *want* it?
- Will they pay for it?

Then it brings more doubts if the concept needs critical mass…

- Will this have enough traction?
- What will I do if it fails to get traction? Kill it? Downgrade it? Change course?

Today, regarding my current project, I am slightly above the red line in your graph, nearing the “Informed Optimism”. I start to feel great now, with a sense of achievement, but I’ve been down in the s*it for several times…
.-= Rui Curado´s last blog ..The Hidden Costs of Domain-Specific Languages =-.


stevew February 21, 2010 at 10:10 pm

Rui – thanks for your honest feedback – I suspect the critical mass question will be an issue for me in due course, and you always wonder how long you have to stick with something before it begins to get traction. I wish you every success with your ABSE initiative!


ibagrak February 23, 2010 at 8:56 pm

Well put. Going through some of these cycles right now.
.-= ibagrak´s last blog ..On private joys of ownership =-.


Masha Petrova March 3, 2010 at 5:09 pm

Hi Steve,

Good post! So good to hear that I am not alone on the emotional entrepreneurial rollercoaster.
I was in the pessimism stage when I wrote this post:

Thanks for sharing!


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