A key tension in ideation, and bossing yourself around

“As a second-time founder, where do I find the idea for my next company?”

In my last post, I explored the challenges that second-time founders face in ideation. Today, I want to focus on a tension in the process that many overlook: the balance between confidence-building and self-discovery. Let me break this down.

As a second-time founder, your ideation process moves down two paths simultaneously:

The need for confidence-building emerges from the multitude of options available to you. You naturally care about the quality of your choice between them. Success means not only reaching a good outcome, but trusting that it is superior (within reason) to the alternatives. This trust is the confidence you need to build.

Many founders approach this need by being methodical and principled about their decisions, creating a focus on process.

Self-discovery comes from a different source. By this point in your life and career, you’ve accumulated unique interests and passions. These suggest directions you could explore for your next venture. Every experienced founder I’ve met has several of these intuitive pulls, and most have one they’re particularly drawn to.

The tension

Process provides comforting stability, but makes trusting your intuitions difficult. These inner nudges simply resonate with you – they didn’t emerge from careful reasoning, and may lack clear justification. Can you, and should you, prefer them?

This question is trickier than it appears. Unlike my description, intuition’s “call” can initially be subtle. Recognizing these signals requires a high level of self-awareness and reflection. Many founders dismiss them as no more than “unrealistic dreams”.

This is where finding balance is critical. Consider the flip side: can you afford to dismiss your dreams? 

Your choice will shape your world for years to come. It will dictate the work you do, the people surrounding you, even the thoughts occupying your mind. In other words, your decision has strong identity implications.

As a founder, you have the privilege of choosing this element of your identity. Yet principled decision-making processes often fail to account for these deeply personal considerations.

Moving forward

I’ve seen the full spectrum of outcomes coming out of this tension. Some founders explored their passions, but ultimately found no viable ideas and moved on. Others, despite having great “traditional” startup directions, chose ideas with “limited” potential because they cared deeply about them. And there are many options in between. 

What doesn’t work, however, is ignoring this tension altogether.

Committing to your next venture means choosing the potential of one idea, at the cost of giving up all others. With numerous options, your alternative cost is high. Founders who never consider pursuing their passions aren’t, typically, ready to make this commitment.

This doesn’t mean blindly following your original intuition. Passion for an alternative can often be developed, by choice, at a later point. It doesn’t even mean spending extensive time exploring your intuitions before moving on. There are valid reasons for choosing otherwise.

But you must respect this part of your identity by being intentional: acknowledge the road you might not take, and if you move past it, do so by conscious choice. That choice is the point of balance – where process and intuition combine to guide you onwards.

Short Thoughts

How good are you at bossing yourself around? A mental model of self-direction

Founders don't have bosses - they must direct themselves.

They’re not alone - this characterizes many entrepreneurial paths (including small business owners and freelancers). Self-direction is also required of some people who do have bosses (such as academic researchers, and many leaders), and is common in anyone’s non-work life.

The extent of self-direction depends on the development stage of a business, role, or project.

When you’re just starting, the level of uncertainty tends to be very high, making self-direction more prominent.

Later, as things start taking shape, more and more is defined by the routines that develop.

What makes this harder is that often, a new founder (or freelancer, professor, department head, parent...) doesn't know what they’re doing, and needs to figure it out. For most, the extent of available support is limited. The early phase, therefore, includes an additional self-guidance challenge, for learning what you’re doing in the first place.

These processes - of figuring out what you need to do, prioritizing, and making decisions, are resource-intensive. People rarely, however, account for the time, attention, and energy they require. We don't tend to think of "figuring out what I need to do" as a task in and of itself. When it reduces the availability of resources for other purposes, you feel something is wrong. Are you less productive, slow, or stuck?

These concerns become a source of stress and self-doubt. There's no way around them, though - the price of doing something new is learning how to do it.

Having this mental model helps you understand what you're going through. You can't predict how long you’ll be learning, but by anticipating the initial challenges, you can regain some of your calm.

Coincidentally, this is often the source of the stress and frustration that second-timer founders feel in ideation. When you feel this way, slow down. Judge your progress relative to realistic expectations, which account for starting with no idea what you’re doing. You’re probably doing better than you feel.