The Hardest Part About Being a Founder

Olivia Wong
Prototype Thinking
Published in
6 min readJun 25, 2019

Navigating constant uncertainty? Here’s what to do about it.

Photo by Victoria Heath on Unsplash

One of the hardest parts about being a founder is that we’re constantly living in a state of uncertainty. There’s a perpetual state of low-lying stress that never seems to go away. We wake up each day not knowing if our business is going to work out, if we’re able to pay our employees next month (let alone ourselves), and if we’re even doing the right things.

I recently asked a group of 30 other female founders what they thought were the hardest parts about building a company and here’s what a few said.

“It feels like there are 100 important things to do at every moment of every day and that many of them rely on each other. When your budget is tight, your team is small, and you’re really just proving a concept and getting started, its such a challenge to disentangle this knot of things to do and stay focused and just chip away at it.” — Alison Mountford, Founder of Ends & Stems

“Uncertainty. You don’t know if it is going to work out and whether all the efforts you spend are going to result in a positive outcome and not one big disappointment.” — Julia, Founder of Ostelia

“The hardest thing is prioritising when under stress. People always say “Just pick the most important thing and do that! Simple, right?” — Tes Macpherson, Founder of PTAsocial

I can totally relate. When we’re just getting started, the sheer number of things to do can feel dizzying. Where do I start? How do I put the right team together? How do I get my product or service off the ground before I run out of money? No matter how long you’ve been in your business chances are, you are and will face uncertainty. So if it’s us against uncertainty, then our main objective should be to solve for uncertainty.

I believe our top task as founders is to become experts in learning and managing our own learning curves. We need to get good at solving problems we don’t have the answers to and we need to learn how to do it quickly. At my company Prototype Thinking Labs, we’re obsessed with learning. We’re fast at identifying what we don’t know and rely on a set of techniques to increase our speed of learning.

As a co-founder of a consultancy whose main expertise is teaching other companies how to de-risk their business, here are 3 pieces of advice on how to learn fast and increase your aptitude for uncertainty.

1. Start by ranking your biggest uncertainties about your product or service.

Take out a sheet of paper and write down all of your biggest risks, unknowns, uncertainties, and assumptions. Next, rank them in order of importance. Your top unknowns are the ones that are most important to solve but you are the least sure about.

For example, say you’re building a financial planning app for millennial couples and your top uncertainty is whether people will download your app. Your #1 risk might be “will people want our product” followed by “will people download the app”. If you’re building a new line of organic ayurvedic skincare, your top uncertainty might be “does our product resonate with our users” followed by “will they buy it”.

Here are the top risks for a mobile app idea called “Buycott”. The app allows shoppers to scan bar codes to identify unethical products and find sustainable alternatives.

Have each member of your team do this exercise and compare answers.

Ranking risks is a great exercise to use whenever you’re feeling lost and don’t know what to do next or when you’re stuck and not seeing the results you’re expecting. We can’t move forward until we’re clear on what we don’t know. Only once we’re aware of our tops unknowns can we create a plan to solve for them.

2. Run experiments to test each unknown.

If you want to know if people can understand your product or service, quickly sketch a piece of marketing material and get feedback on it. For a mobile app, you might sketch out a Facebook ad or the product description in the App store. For a product like organic skincare, you might use an empty container and tape a piece of paper around it with a list of ingredients.

This works just as well for a service. Say you have an idea to create an upscale concierge service for C-Suite Executives. You could sketch out a landing page and run it by an Executive Assistant. As much as possible when building your prototypes, be concrete and specific but don’t be afraid to guess. Someone should be able to interact with your prototype as if it were real (ie. don’t use squiggly lines to represent text). As much as possible, we want to preserve our user’s ability to give us their immediate, authentic reactions. When we make them fill in our missing blanks, we force them to use their creative brain rather than their reaction brain which is not ideal because it can comprise the quality of the data.

In our live workshops, we teach founders how to test everything from marketing campaigns to concert experiences and internal workflows. You don’t need to wait months for a functioning MVP to get key validation information. Start by building a paper prototype, flyer, or landing page.

3. Stay in the realm of paper & make live iterations during your user test.

Don’t wait until after a test to make an adjustment to your prototype. If something isn’t working for your user, use your intuition to fix the prototype in real-time. Just pause the test, make your revision, and put the prototype back in front of your user. Have your user interact with the updated prototype as if the new changes were always there. If you’re prototyping a service instead of software or a physical product, you will use a combination of paper and roleplay.

Flag-size stickies are perfect for making quick edits.

(A quick note on paper: a common question I get from founders is why we prefer using paper over using digital tools like Invision to sketch our designs. We work exclusively with paper prototypes at the earliest stages of development because paper allows us to make changes at the speed of thought. It’s much easier to make iterations on paper during a user test than it is to update a digital mockup.)

If you’ve never seen someone make live iterations during a test, here’s a video of an example user test.

Keep Going.

Building a company can be painstakingly hard. There will always be a never-ending list of opportunities, directions, and ideas to pursue. And there will never be a simple or right answer. Don’t let this deter you from seeing your dream through. The best entrepreneurs I know are the ones who don’t back down when times are hard. They keep going, beating their arms against the current until the wind catches up with their sails.

Despite the sheer amount of pressure and risk this profession entails, I wouldn’t have it any other way. Without risk, there’s no reward. A founder’s journey might be an upward battle but what’s life without a good challenge?

Want more specific tactics for experimenting & testing? Feel free to hit me up at Prototype Thinking Labs.

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