Entrepreneurs Should Dream About the Future But Operate In the Present

Entrepreneur Office Hours - Issue #258

Around this time a year ago I was meeting with an entrepreneur, and I remember her being stressed trying to plan her entire startup journey. Fast forward a year, and it felt like she’d done a complete 180. She was telling me how she understood startup life is unpredictable. She talked about how any time spent imagining how your startup was going to be in the future is nothing more than wasted time. And she kept referencing the importance of embracing opportunities as they arise and living “in the moment.”

I couldn’t help but smile as I listened because it’s a lesson I try to impart on all the entrepreneurs I meet. Entrepreneurs fall into the trap of thinking we can somehow predict the future. We outline every step, project every scenario, and convince ourselves our plans will keep us safe from surprises. But that’s not how this career works. Entrepreneurship — and life, in general — is a chaotic, unpredictable ride. The more we try to control every detail, the more we miss out on the opportunities that come from adaptability and spontaneity.

Simply put, not spending all your time trying to predict or control the future can be incredibly liberating. It allows you to stay focused on what you’re building right now, with the awareness that plans might change, and that’s okay. This approach gives you space to be open to unexpected possibilities — maybe a new partnership, an unplanned pivot, or a sudden market shift. And those kinds of things are important in part because many of the most successful ventures in history are the results of people spotting opportunities they didn’t originally see coming.

To be clear, I’m not suggesting you shouldn’t have dreams. Dreaming big is great… especially as a source of motivation, and you certainly don’t want to settle into thinking life’s unpredictability means giving up on your biggest goals. Instead, you should be focused on balancing that dream with a grounded sense of practicality. Dream big, but don’t confuse your imagination with reality.

Ultimately, your entrepreneurial dreams are a guide, not a blueprint, and entrepreneurship is about finding the balance between having vision and being adaptable. So, yes, dream big. Envision the future you want to create. But be prepared to embrace a bit of chaos while letting go of the idea you can plan your way to success. Doing so will ultimately create the perfect mindset for the wild, wonderful, and unpredictable journey that is entrepreneurship.

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Podcast: ThoughtWave Episode #4

Why Customer Choices Are Like Votes, AI Changes Search, and Wearable Tech is the Next Frontier

In this episode of ThoughtWave, Dr. Aaron Dinin and Chris Leithe break down the real business lessons behind the most surprising, yet overlooked, part of our daily choices—whether in the voting booth or the marketplace. They dive into how customer decisions are like votes, evaluating which product or brand offers the most immediate value. From analyzing campaign messaging strategies to exploring the importance of audience building in the era of AI-driven search, Dr. D and Chris give you actionable takeaways for communicating value and staying relevant in an evolving digital landscape.

Listen now on: Apple | Spotify | Online

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This week’s new articles…

Growing a Business Requires Ignoring the Kinds of Things Entrepreneurs Love Doing

The entrepreneurs who ultimately achieve long term success are the ones who know how to prioritize the right type of work.

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The First Step Toward Becoming an Entrepreneur Isn’t What Most People Think

And, more importantly, the first step definitely doesn’t require submitting any sort of official paperwork with the government.

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Office Hours Q&A

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QUESTION:

Hi Aaron,

I feel like the following is a somewhat silly problem, but it’s what I’m feeling and I need help solving it from someone whith a perspective beyond my social or entrepreneurial bubble.

Here is the issue: As my startup grows, I’m starting to feel overwhelmed by the number of decisions I have to make every day.

I know decision fatigue is a real thing, but I don’t think I appreciated just how big of a thing it is in startups, and I have no idea how to manage it effectively.

Do you have any advice on how to handle the constant decision-making without burning out?

Kindly yours,
Sage

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First, I want to point out that this isn’t a silly problem at all. In fact, decision fatigue is something almost every founder faces, but it doesn’t get nearly enough attention. As your startup grows, so do the decisions — big and small. And, because it’s “your startup,” lots of people are afraid to make choices without you being involved, so they’re constantly coming to you. As a result, the constant need to choose absolutely becomes overwhelming.

One approach I’d recommend is setting up a framework for recurring decisions. Identify the routine decisions that pop up daily, like approving expenses under a certain amount, scheduling meetings, or greenlighting minor product tweaks. Wherever possible, create default answers or criteria so you don’t have to think about them every time they come up. Even something as simple as blocking out set times for decision-making can help give your brain a break during the rest of the day.

Another tactic that’s helped me a lot is delegation. I realize letting go of control, especially in a startup where every detail feels critical, is difficult, but if you’re handling everything personally, you’re going to burn out. Start by giving trusted team members ownership over areas where you’d typically make the final call. You’ll have to invest a bit of time upfront to train and trust them, but once they’re handling those decisions, you’ll have freed up your mental energy for the bigger, strategic choices.

Finally, prioritize your decisions each day. Tackle the big decisions first while your mind is fresh. Lower-priority decisions can wait until later or even be deferred to another day if they’re not time-sensitive. This way, you’re always putting your best mental energy where it matters most.

Oh… and one bonus piece of advice I recently heard from a founder is to figure out how to train your employees to make the decisions you’d make. By teaching employees to “think like you,” you’ll create a company of people capable of making decisions you’d approve of.

To be fair, I haven’t tried this last suggestion myself; however, it feels like it could be good advice, so I wanted to share. Just don’t blame me too much if it sucks… =)

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!