Seven Dilemmas for First-Time Entrepreneurs


Any meaningful AND significant pursuit will involve a huge learning curve.

Some pursuits are “safer” than others as your long struggle can be private before you ultimately expose yourself in public. Examples of such pursuits are some kinds of music or some kind of sports where a large part of the training can happen in private.

Entrepreneurship, however,  is a largely public sport. To gain real traction, you have to touch several stakeholders in public. So, you are “exposed” from the word “Go.”

With the above in context, here are seven dilemmas you might face as a first-time entrepreneur

1. The lure to get back to past certainty vs the grit to persist under uncertainty

In general, your past has a HUGE amount of certainty as you probably were working for someone and you were pretty good at what you did. On the other hand, your future as an entrepreneur has a HUGE amount of uncertainty. Any one thing that goes wrong in your entrepreneurial journey can derail your project and close that chapter. Since the combination of the “project” and “YOU executing that project” is extremely unique, there is no precedence to draw upon. Analogies will only go to a certain extent.

Your grit to persist under uncertainty has to outweigh the lure to get back to past certainty for you to continue on the journey.

2. The choice to stretch and do it alone vs the choice get good help

There are times when you should stretch and grow to meet the escalating challenges of building a startup and there are times when you should aggressively reach out for good help. The former is your road to maturity as an entrepreneur and the latter is your road to maturity to build a strong ecosystem. Both – your personal growth and the growth of your ecosystem are important.

What is more important is the choices you make at every crossroad. If you make the wrong choices, you either rob yourself of much needed personal growth or you grow up as lone ranger and ultimately reach a point where your personal competence limit will limit the growth of your venture.

3. The question of sharing

The “sharing about your startup” question is an important one.

On one end you can adopt a “seal your lips” attitude and on the other end you can adopt a “throw the kitchen sink” attitude and of course you can play the game anywhere in between the two.

Sharing about your startup always comes down to:

  • What are you sharing – just the vision or the intricate details of how you will realize it
  • With whom are you sharing – anyone and everyone or a select few
  • When are you sharing – at major milestones or throughout the journey
  • How are you sharing – casually without any design or in a formal fashion

And most importantly…

  • Why are you sharing – are you doing this purposefully or mindlessly.

Unless you revisit the question of sharing in-depth and have a strategy, you will end up having a lot of activity with limited productivity because you will waste time for both you and the person on the other end.

4. You vs Them

Actually, it’s not simply “you vs them” but the slice and proportion of attention for your projects as compared to the slice and proportion of attention you set aside for their projects. When you are building your first startup, you are always hungry for any kind of resources and every connection looks like a possible piece of your startup puzzle. It is tempting to “use” anyone and everything that come across your way to further your quest. On the other hand, people that you meet are not simply cruising through their lives. They have their own projects too and rightfully so they may be seeing you as a puzzle piece to further their quests.

Rather than struggling with this, increase your capacity to move the needle for others quickly and at a low cost to you. Rather than expecting them extend their hand to help you, reach out to them with a helping hand first.

Reciprocation is a powerful thing and the fastest way to activate that power is to proactively reach out and help others with their quests.

5. Crafting a great story vs making something that is worthy of a great story

If you think coming up with an idea is hard, you have not experienced what it takes to execute one. Without blood and sweat, you can’t create something that is worth talking about. On the other hand, if you don’t know how to craft a great story about what you are trying to build, what you have built or how you are going about building it, you can’t get all the desired traction.

Balancing superb execution with flawless storytelling is a must to make something meaningful happen.

6. Going for a home run vs focusing on a series of singles and doubles

There are two schools of thought – one is to go for the “home run” so that you can get “backing” from serious people and the other is to go for “singles and doubles” to prove yourself first and then grow from there.

There are advantages and disadvantages of both of the approaches and you don’t have to pick one over the other as it is a “black vs white” choice. Your goal should be able to paint a grand vision while having a “staircase to heaven” execution approach. People should be able to see the vision at the same time believe that you have a plausible execution plan that

Remember: If people don’t believe you, they rarely tell you about their disbelief. Their supporting actions after the meeting are a good indicator of how much they believe in you and your plan.

7. The signal vs the noise

This is probably the simplest to understand but the hardest one to remember throughout your first entrepreneurial journey. There is an abundance of information about how to go from where you are to where you want to go. You will also find enough people to give you advice of all kinds. You owe it to yourself to gain enough wisdom to be able to separate the wheat from the chaff and be able to do so very quickly.

Your inability to distinguish between signal and noise will cost you way more than consuming that information. Why? Because every wrong turn in your journey will add incremental costs to recover and get back on track.

Have a great week ahead.