Lean into the fear: how to deal with uncertainty & doubt in a startup environment

Rockman Law
7 min readSep 18, 2017
Photo by Joe Beck on Unsplash

“Doubt is not a pleasant condition, but certainty is absurd ” — Voltaire

I am pretty sure when Voltaire said this, he wasn’t referring to start-ups but it is the perfect analogy of what it’s like working in one. There will be a lot of doubt and unknowns; will I run out of money, have I got the right product/market fit, will my competitors crush me and many more but you would be fooling yourself to think you can eliminate uncertainty from the equation.

That’s not to say there aren’t ways to deal with it, here are a few observations and things to try out:

Photo by Yeshi Kangrang on Unsplash

Don’t fall into Analysis Paralysis —When you are dealing with uncertain situations, a lot of the time your early assumptions of the problem will be wrong, no matter how much data you try to collect. So the only way to really know is to just do it; build it, test it on real users and customers so don’t spend too much time overthinking it. Remember not to let uncertainty lead to fear; fear of the unknown, fear of getting it wrong, fear of failure or you will get stuck in this endless loop of analysing it, debating it, coming up with 20 options and never starting.

Real Life Example: This year we were invited to join SwiftScale, a programme connecting scale-ups with corporates to explore commercial opportunities. Because there was a substantial one-off fee upfront, we weren’t sure we would get a ROI on this. Instead of spending lots of time debating or analysing it, we called some of the alumni from the previous cohort and got their feedback, then calculated we only needed to close one Proof-of-Concept project to make a positive return so we just went with it and it’s been a good decision.

Comfort in doubt — Hate to break it to you but doubt never really goes away, no matter what stage your company is at. Sure, the level of uncertainty is a lot higher the earlier you are as a start-up but I can imagine the bling bling unicorns still wrestle with this (see SoundCloud). It’s important to get comfortable with the “I am not 100% sure whether it’s right but its probably not too far off” feeling. Accept the fact that you will never have enough data to make decisions (sometimes even key ones) in a start-up. From my own experience, particularly at the early stages, the best balance is usually a combination of some data and a gut feeling.

Real Life Example: When we started SQR Systems, we didn’t know what the application of the technology would be, only that it was a great piece of technology. But it was okay to feel that doubt and take the leap because we were confident we would eventually find the right product/market fit.

Photo by Håkan Dahlström

Connect the dots — Most of the time when you are faced with big, complex problems it’s difficult to know where to start. Try identifying things that make sense to you and build from there. And after that there may still be lots of seemingly unrelated pieces of data and you will have no idea what they mean on their own but patterns will emerge if you start connecting the dots. Much like a connect-the-dots puzzle, the picture will eventually reveal itself to you if you connect enough dots and hopefully before you run out of money or your competitors overtake you, which is why the next point is important.

Real Life Example: When we first started developing the technology, we didn’t know it would turn out to be Ceerus, a secure communications platform for mobile and IoT data. Back then the aim was to build technology to protect data over different networks and devices without breaking the encryption. That was it. We built secure video transmission systems, experimented with new key management techniques, ported our code onto a Raspberry Pi and developed new ways to compress and transmit securely target regions of a frame in high quality while suppressing the background. But all this time, we made a conscious effort to keep connecting the dots, and trusted that it would become something more.

Photo by Joshua Ness on Unsplash

Go fast and zig-zag — Now that you’ve got a good idea of where the destination is, pick a path and go as quickly as you can. You won’t always get to your solution on the first try so it’s important to take pause, see what data you have collected on the way, validate it (with customers, users or people who have encountered the same problem before) and then make corrections if it looks like you are veering off-course. And because you are executing rapidly in small increments in a particular direction, you can always re-calibrate and course-correct without causing too much damage, in terms of resources wasted or time spent.

Real Life Example: In the beginning we thought our market would be in broadcasting, helping content providers protect their video streaming. When that didn’t work, we pivoted to developing secure video transmission software for CCTV cameras. When that didn’t generate enough traction, we pivoted to providing enterprise and Government organisations flexibility in how they control their data and how they manage their keys to meet regulatory compliance. Now we see huge potential in the IoT market so watch this space.

Collect data, the smart way— At this point you may be well on your way to uncovering the murder-mystery that is your uncertainty but it’s worthwhile to consider having a system in place to collect data. This is because having the right structure helps you to gather and sort data quickly, and even better if you can automate this process because then you just wait for the data to flow in, you will always have data to make decisions and not waste time gathering it.

Real Life Example: At the start of the year, we wanted to find out how happy our employees are in the company. We knew we wanted to keep it simple but still collect useful data so we created an online form called the Happiness Survey and sent that to our employees every month to gauge their level of satisfaction. The responses are sent back to us anonymised and the results tabulated in a spreadsheet. This meant we can see the trends month-on-month and we have the data right there if we need to take action.

Photo by Cristian Newman on Unsplash

Freaking out — It’s okay to freak out sometimes. I actually think it’s good to get it out of your system but don’t stay in this zone for too long, as after a while it’s not constructive. It helps to have a good support system around you whether it’s your team or someone in your personal life so you can work through it. Basically have someone (relatively) sane around you when you are teetering on the edge of madness. Now I’m not saying that those people won’t try and strangle you when you’re acting all crazy but they can bring perspective when you’ve lost sight of it.

Real Life Example: I can give you so many examples of this, from that time we lost a massive Government tender because of factors outside of our control, to the first time we pitched to a VC and they ripped us to shreds, or the time we had to restructure the company and let people go or the many times we thought we did enough to win the contract only to be rejected late in the game. After each and every one of those experiences, we allowed ourselves some time to process it, we dusted ourselves off and came back stronger.

In the end there is no easy way around dealing with uncertainty, you just have to embrace it. That’s the entrepreneur’s life. After a while, it’ll become second nature and you’ll freak out less, make decisions faster, and pivot quicker. Just like the wise and powerful Sheryl Sandberg once said “Lean in” but to add to that I say “Lean in-to the fear”.

--

--

Rockman Law

Venture scout, angel investor and recovering founder