Help Me Answer This Deep Question From a Young Entrepreneur

What would you say to this question? I think it’s too deep for me to answer by myself. Please join me in the comments, with your answer. 

Here’s the question: 

I have an idea that I am hopelessly passionate about, but I question the wisdom of trying to execute at this point in my life. I’m young and inexperienced. I’ve started companies in the past, but they were barely minnows. And my passion is to build something truly special, with longevity, that adds real value to life. In other words, it’s a whale of a project.

I’ve asked myself a thousand times, and I sincerely do believe I can do it. I’ll surround myself with people smarter, better, and greater than me who share my vision. Collectively, I truly believe we could do it; but I also know I will make innumerable mistakes a long the way; many of which I could potentially avoid with more experience. My rational brain tells me to continue to learn and make mistakes under the shelter and guidance of others. Learn to be a better leader by following first. But I’m consumed by my idea. I’ve tried boxing it up, putting it in a safe spot to be dusted off later – but I fail hopelessly, each and every day. I’m just not sure what to do.

So I guess where I could really use guidance is: is my uncertainty a sign that I’m not ready? Were you ever uncertain about your timing or level of experience?

And my answer is:

First: No uncertainty is not a sign that you’re not ready. Uncertainty is an indication of intelligence and understanding. I mistrust certainty in almost all areas of life. People who are sure of something probably don’t fully understand the something. 

Second: Yes, I’ve been almost always uncertain about timing and I still am. As for level of experience I am very confident in my areas of expertise but I also remain very respectful of what I don’t know. 

But please help. Add your answer here as a comment. You know as much about this as I do. 



  • webpage says:

    Do you have any video of that? I’d love to find out some additional information.

  • Allan says:

    Create a research and reading habit, maintain it for as long as you can.

    Then you will find that things that seem like whales, you just laugh at and avoid, because the whale is surrounded by hot mermaids or mermen, about a billion of them.

    You’ll no longer fear mistakes or failures because by the time you take action, you’ve made a trillion of them in your mind. In the time it takes to read a sentance. A brilliant quotable sentance.

    That about covers it I reckon.

  • Jeremie Averous says:

    I love this post and the question. I just launched my own startup. And my answer is:
    You will never be ready. Don’t wait until you’ll regret not to have done it. Of course you need to have a plan that involves a little bit of risk mitigation – and most importantly don’t start alone.
    I would hazard a launch suggestion: get 2-3 great people that will share your dream onboard and once they are ready, jump for it. You’ll have the team, you’ll find the way.

  • Warren Rutherford says:

    Tim – your 2nd point is crucial in answering the first. You are very certain in your self direction, have clear significance in your role awareness, and are quite connected with your belief in self – your expertise. Thus, the uncertainty of the decision is not uncertainty inasmuch as it is your systemic process kicking in, analyzing the alternatives, weighing the risks, and then determining the course of action. Nice post.

  • Doug Hedlund says:

    If you’re a know-it-all who won’t ask more-experienced people for help, then don’t go for it. (However, your question indicates that you’re smart enough to know what you don’t know, and ask for help.) Here’s one entrepreneur’s reflection: I got an Ivy-league MBA and worked for big-league consulting firms for nine years before launching my dream-business. Soon after, I realized that I didn’t really know how to run a business until I had my own. So–get sufficient capital to give your business a reasonable time to get traction…aggressively maintain a healthy Gross Profit Margin…be big enough to ask good people for advice…and don’t spend on anything that won’t generate short-term revenue until you reach break-even on a cash flow basis. (Until then, you won’t know if you’ve got a business.) Kindest good wishes to you!

  • Travis Bishop says:

    ” Uncertainty is an indication of intelligence and understanding. I mistrust certainty in almost all areas of life. People who are sure of something probably don’t fully understand the something.”
    — Tim Berry


    If there’s a hundred bolted doors, and success is behind only one of them, 95% of people are gonna stand there thinking of the right one to pick, while an entrepreneur is going to get busy getting the first 56 doors wrong.

    There’s no ‘right time’ to spend thousands of dollars of your own money working 60-70 hours a week. The longer you wait, the more comfortable you become with regret. I went part-time in college with only 20 credits left, which most people thought was stupid. But most people don’t start companies, most people don’t like leaving their comfort zone, and most people would rather feel mediocre than feel like a loser for more than ten minutes.

    What do you think about when you’re laying in bed at 2am? Unless you’re working for and/or learning from other entrepreneurs in a related field, I’d say learn from the mistakes you make going after your goal.

  • Mike Fourcher says:

    When addressed with the question of whether or not to do something (that isn’t life-threatening), always do. The key to life is exposure to new experiences and the more of those you obtain, especially failures, is the key to long-term success and happiness.

    As a corollary, the sooner you are able to define success by your own terms, as opposed to terms given to you by others, the sooner you’ll find happiness.

  • "The Young, Uncertain Entrepreneur" says:

    All –
    I can’t thank you enough for your incredibly thoughtful advice. Up until reaching out to Tim, I had cowardly internalized my questions. I was caught up in stories of success that were written with such clarity and elegance that fears, uncertainties and doubts seemingly amounted to no more than a footnote. I didn’t question because I was afraid my uncertainty would convey weakness and a lack of confidence and conviction.

    It’s reassuring to know I’m not to alone. And that uncertainty is not only natural but also quite healthy. This is the feedback I was so scared to ask for, yet so desperately needed. Thank you : )

    In terms of next steps, I’ve decided to spend the next four weeks aggressively – yet thoughtfully and open-mindedly – trying to validate my idea. @Cliff – I’ll reach out to the smartest and most experienced people I know and soak up their wisdom and guidance. @Charles – absolutely, this can be diced into smaller, more digestible goals. The concept deck I have put together breaks my “whale” of a vision into three progressive stages, each building on the last. And at each stage I will iterate until validation (question, build, prove – rinse and repeat).

    Again, I can’t thank you all enough. I would love to keep you all informed; if you’re interested, I will certainly trouble Tim with substantive updates. And who knows… maybe 5, 7, 10 years from now, I will have played a role in helping build something truly meaningful and lasting.

    Onward : ),
    The Young, Uncertain Entrepreneur

  • Carlos Diaz says:

    I have seen many people with the same question, which is basically: Am I ready now to take the plunge into the unknown of being a 24/7 entrepreneur. My answer is always: If the passion is there, and you consider yourself ready for a period of intense disappointments and rewards, go for it. If you still are not sure about your idea, financial security and basically if your idea is solid enough for a self-sustaining and profitable business….keep on researching and studying until you feel sure. The idea in your mind has to be ready to be documented, discussed and defended in a professional environment.
    A local note: We are planning to address this particular dilemma in a workshop called MyIdea=MyBusiness (in Spanish, Midea=MiNegocio) that another entrepreneur-professor like myself are starting next month. More about this for the bilingual readers of your blog:
    Carlos Diaz

  • Sampathkumar Iyengar says:

    Think Positively and Rationally and Give your best. You should come out trumps
    ” Trial Costs Noting, but brings in rich Experience”

  • Emmanuel Shadrack Opiyo says:

    The 1st thing I always ask myself every moment an idea pops into my head is how far I can believe in it.Then the next question bits in,where the idea will it take me if i decide not to give it a try.

    The worst mistake any entrepreneur will commit to, is accepting procrastination to rule his growth.To this I speak boldly “don’t do it tomorrow and fail,do it today and you will still have time tomorrow to rectify it by just doing it today”.and remember believe in it to understand its worth.

    All the best

  • Anne Maxfield says:

    I agree with Charles and would add that being certain about taking on a venture is probably more dangerous that being uncertain. When you’re uncertain you’re open to thoughts and opinions that you would probably ignore otherwise.
    Take the risk, be the whale, prepare for success! And know that no matter what, you’ll figure it out.

  • Charles Robinson says:

    Sometimes you just have to do what you have to do. You can’t rationalize it to yourself or anyone else. I am exiting the I.T. industry in about six weeks to focus on my passion in the culinary arts. I don’t know where it will take me, and I don’t even know exactly what I will be doing. I just know this is what I have to do, and now is when I have to do it.

    Regarding the question at hand, can this be be carved into smaller bits and executed incrementally? Start with a dolphin — lean, agile and intelligent — and evolve into the more wise and expansive whale. Another thing to consider is the worst case scenario. Ultimately what’s at stake if it doesn’t go as planned?

  • Sajid Husain says:

    There’ll never be an age where we can say ‘Now I know it all’!

    As long as you are passionate about the idea and you’re sure that this is what you wanna do, then you should do it as soon as possible. I agree with both the points mentioned by Tim as well. Uncertainty is a sign of maturity that you know the risks and it’s not just the exuberance of the idea of starting itself.

    All the best to the entrepreneur…

    …… @sajid_v

  • Cliff Elam says:

    I would suggest that he work through the idea with as many smart people as he can get his hands on AND try to time the marketplace a bit. No matter how good the idea is, if it’s coming into the capital markets when there is no appetite….


  • Jeff Huckaby says:

    1. Uncertainty is an indication that you are concerned about risk. This is healthy and smart. Many business functions revolved around reducing risk. Appreciating risk-reward is a key element to managing a start-up

    2. Timing is a highly personal choice. Sure there are economic issues to consider (these are risks), but more importantly do you have the financial, time, emotional and physical resources to start something.

    3. Recognizing that you need people around you who are more experienced than you is the best experience any founder needs.

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