Why ideation is hard for second-time founders

"I’m a second-time founder. Why is ideation so hard?”

After building your first startup, you may expect (hope?) that things will be easier with the next one. That’s true for some parts of the journey, but often not for ideation. These are the main reasons I've found for that challenge, after discussing it with dozens of experienced founders:

1. Standards – You know the personal price of building a startup (it’s hard and demanding, and as a second-timer, there’s a high opportunity cost). Is it worth doing again? To be sure, you’re probably setting exceptionally high standards for the idea you pick.

   
   

2. Network – Your network is better than when you worked on your first startup. That will be an advantage in just a bit (for market research, validation, and signing design partners). When you’re just starting, however, it can create overwhelming noise. To begin exploring, you’ll probably grab coffee with anyone whose opinion you value: friends, former colleagues, past investors... And they’ll be well-meaning, and most will be insightful. The advice you get will be all over the place. Each suggestion may help in the right context, but how do you pick? To make things worse, some may (even inadvertently!) try to influence you to choose their favorite area before you feel ready. What if someone awesome offers a (truly) no-strings-attached angel check “just because they believe in you”? You have doubts about their suggested direction, and you’re no pushover. They’ll support you even if you go down a different path. But you don’t have a better idea yet, you’d love to be past this frustrating ideation phase, and if they’re offering real money… Maybe they see something you’re missing? This quickly becomes confusing.

   
   

3. Process – Ideation was a small part of building your first startup – and for the next one, you want to run a more thoughtful process. This means your ideation experience is limited (or irrelevant) relative to your current aspirations. You’re raising the bar again: not only for the idea you choose, but also for the process for picking it. A better process will increase your confidence, but it is… harder.

   
   

4. Mindset – You’re used to being in startup-building mode: focusing on goal-oriented execution and prioritizing speed. The skills and mindset required for successful ideation are diametrically opposed – you’ll need to focus on exploration as you work towards an ambiguous goal. There are no clear metrics, you don’t know how close you are until you’re (almost) there, and parts of the process just need time. This conflict makes ideation stressful and uncomfortable for many second-time founders.

   
   

5. Loneliness – People around you don’t understand. They, too, expect your next startup to be easier – and may never have heard of “ideation”. The longer you ideate (and it’s almost always more than you’d like), the weirder they’ll get about it. Your mom will ask why you’re such a perfectionist. Your grandparents may connect you to their neighbor who’s hiring for a (completely irrelevant) tech role. Your partner may lose patience… (all examples from people I worked with, who are not at all me). This is extremely isolating. If you’re ideating with a co-founder, at least you’ll be lonely together… Otherwise, it’s even worse.

   
   

Awareness and understanding are the first steps towards improvement. What can you do to actually move forward? There are no “right” answers, because you’re looking for something new, that wasn’t done before… I have some thoughts that may help, which I’ll share in the next post.

Short Thoughts

When you evaluate what’s happening right now, there’s a human tendency to ignore some of your problems. E.g., you don’t acknowledge a mistake (with consequences that limit you), to protect your self-image, or you ignore a problem if dealing with it is too scary. This doesn’t work. You probably know that, so you focus on being as realistic as possible, and use defense mechanisms to alert you to mistakes (those can also fail, but that’s a topic for another time).

When you create a vision for the future, the most common challenge is to see past the constraints you know, and imagine what could happen if a certain limitation were eliminated. Visualizing such bold ideas is a must if you want to have meaningful impact. You probably know that, so you allocate dedicated time for strategic thinking, and may use tools that spark creativity or a visionary mindset.

These capacities, present realism and future vision, are at odds with each other. When building a startup, you can overcome the tension by building teams: pairing a visionary’s foresight with an operator’s groundedness and executive abilities. In your personal life, it can be harder. Most people have some of each capacity, but excelling in both is rare.

So, are you the visionary or the operator? Do you know? And who will you ask for help with the parts you’re more challenged by?