Conviction vs skepticism: how do you balance the two as a founder/maker?

Talking to customers to solve problems would be one way to see if you are on the right path. Not selling them a solution, but solving a problem they have.

Primarily by talking to the users and studying the competition. The healthy approach is to know your shortcomings. E.g., I am building Instant Video Communication for Teams (async video). It's not going to fully replace standard video calls, and I am aware of that. I focus on the problem I want to solve, but I know I won't solve all of the problems. I also know that I am not ready to serve very big customers as they expect many integrations I can't provide. By being realistic about my potential customer base and my limitations I can also sell better.

Good question Janet. Like any good sales person. A founder should be listening to verbal and non-verbal queues from customers/investors/prospects. While digging into objections as well as interests. Its important to have a close group of people who you share your skepticism with and plan specific experiments to evaluate or test them out.

What a great question! This is probably the hardest part of entrepreneurship. Externally you need to be confident and credible. Internally you need to know your own weaknesses and what to work on in the business. I honestly don't know the answer to this. I'm thinking someone can only get better at it by experience. Struggle more and you'll find "that balance" that works for you. One way to make it easier is probably to not work on projects bigger than yourself. What I mean is that if you haven't built a biz before, then let's start by making something to make $100. Then make $1000. Then make $10000. With this, you're giving yourself room to learn and reflect and grow. The imbalance might not be as crazy. Of course there are people who can skip this approach and do it big, but how many people can be "those people"? I know not me haha!

I honestly think customer feedback will level this balance quite well. It's the antidote to the Kool Aid effect.

Hey Janet, Every time I come up with a new idea I get super motivated and convinced that this idea will be the one. So I rather wait a little before actually working on it. And there are days that I'm not sure if what I'm doing it's valuable at all. So it's super tricky. So, when I'm feeling a little demotivated I try to tackle small tasks just to show up. And when I'm feeling overly motivated I try to wait a little and evaluate if I should tackle that or not. Hope this helps.

“What one needs in life are the pessimism of intelligence and the optimism of will.”
Andre de Staercke. I believe it applies pretty well to entrepreneurship!

It's a question of skills. If you are a good developer , you need a good salesman who will pack your business. Everyone should do what they know best!

I only advice my product when this what they really need and also: follow The No Asshole Rule

Look at your financials. Are the right numbers going in the right directions at the correct velocities? If not, what needs to be adjusted? But, more importantly, I don't think this is skepticism. Knowing your weaknesses and obstacles and being confident that you can find a way to overcome them is not the same as skepticism and it's not the same as blind optimism.