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The Best and Worst thing about being a Founder

In my coaching practice, I run across common questions and themes.  Some of the themes revolve around the question of why being a founder seems way more difficult than you expected.  And while the tech media might make it look like every founder was an overnight success, I want to make sure you know that most of them felt like they were in over their heads for at least a moment.  This post is about one of my favorite reasons why this stuff is just plain HARD!

The best/worst thing about being a founder

Being a startup founder is harder in reality than most people think before they get started.  Some founders are drawn to one of the best parts of being a founder: not having a boss.  The funny thing is that for some founders, not having a boss is also one of the worst things about being a founder.

Let’s face it. Having a boss makes things simple.  Bosses are sort of the Google Maps of work. They tell you what you need to do and when you need to do it. They even tell you the destination that you should enter into Maps.  Sometimes, Maps will give you options on how to get to your destination and will even tell you the difference in the routes (usually in relative time), so that you have a feeling of choice.  But ultimately, all roads lead to the same destination: the one your boss gave you to begin with.

If you arrive at your destination and it turns out to be the wrong destination, that’s not your fault.  Your boss had the responsibility of deciding where you should go. Your responsibility was to get there to the best of your abilities. 

Was your boss doing you a favor?

Bosses provide all sorts of wonderful things that you might never have appreciated.  For example, they often give you deadlines and due dates.  I know what you’re thinking: “deadlines and due dates are wonderful?”  Now that you are a founder, you tell me.  When I work with founders, many of them struggle with two things:  They struggle with setting deadlines and due dates, and then they struggle with staying on schedule once they’ve created them.

It turns out that having someone else hold you accountable to deadlines is often way easier than holding yourself accountable.  Maybe we’ve been trained by those term papers that always had a deadline that some of us barely made.  But when there isn’t anyone to hold us accountable, deadlines often “slip”. That voice in your head says “It’s only a few days…”.

Another “gift” from bosses is prioritization.  What you don’t often realize when you have a boss is that there may be 100 things that you need to get done over the course of the year.  You don’t realize it because your boss is usually the one that decides what you should be working on right now. They’re prioritizing for you. They are looking at everything you could be doing and giving you the filtered list of what you should be doing at any given time.

Too much choice can be overwhelming

One of the last and biggest gifts that you get from your boss are “lane lines”.  Your boss gives you a limited scope of responsibility.  For example, you are responsible for marketing a particular product line, or selling to particular clients, or managing certain people.  When you have a boss, you might crave more. More power, more responsibility, more scope.  As a founder, you now understand the saying: “Be careful what you wish for”.

In summary, bosses:

  • Tell you what to do
  • Tell you what the destination is
  • Give you deadlines
  • Limit your scope

So is having a boss better than being a founder?

Not necessarily.  But having a boss and being the boss are two very different things. You should expect that making that transition can be challenging.  For example, without a boss, we have to take on a host of new decisions that we formerly took for granted.  And those decisions carry the weight of success or failure with them.

For starters, you have to decide: 

  • What the company is going to make…
  • Who the company is going to serve…
  • How the company is going to make money…
  • How it’s going to create its product/service…
  • And a thousand other details that will be the foundations of your success!

These decisions, in aggregate, will become the “destination” you need to enter into Maps.

But wait! There’s more…

Once you decide the destination, you have to essentially build the vehicle to get there.  And this doesn’t mean that you get a box of vehicle parts labeled with instructions like something Ikea would do if they made cars. It means deciding what vehicle you want, determining what parts you need, and how you need to assemble them.  Think “random Ikea parts with no instruction manual”.

Next, you need to set deadlines for this heap of uncertainty.  The first version of the vehicle will be ready by “x” and the destination will be set by “y”.  We’ll assemble a crew in the next 30 days and we’ll get the money for the trip in the next 90 days.

Without a boss, it’s up to you to decide what tasks and projects have priority. After all, you have limited time, limited personnel, limited money, and an unlimited list of things you “could” do.  So you have to determine where your time and resources can be most effectively spent to help you meet your deadlines and get to your destination!

And last but not least, as the founder, you are responsible for all of it. Yikes!  And did I forget to mention that when you have a boss, you don’t have to figure out how to pay for it all or have to find investors?

So if you are wondering why starting a company has seemed harder than you thought, maybe this will clarify things.  You should also know that you are not the only founder feeling like this founder gig is tough.  But, as the saying goes: if it were easy, everyone would do it.

So how do you make it easier? 

Don’t try to do it all by yourself. 

  • Recruit a strong team that can help you figure out the destination and that you don’t need to micromanage  
  • Look for advisors, mentors, and coaches
  • Speak with other founders and find your brain trust
  • Find the types of investors that can help you navigate the decisions, not just give you money
  • Remember that you are going to get a lot of decisions wrong. That’s part of the process.
  • Commit to learning from your wins and losses everyday

Being a founder is tough. It’s an emotional rollercoaster. It’s also very fulfilling when you get it right.  Acknowledge that it’s difficult, make mistakes, and then get it done.  If you find yourself struggling with any of these things, let me know, I’m happy to help.