9 Dos and 2 Don'ts for Creating Success in Business (and Life)

Every day, hundreds of thousands of blogs are started, thousands of books are published, and hundreds of businesses are created.

The majority don't last.

So what separates those that last from those that fail?

The ones that succeed - do they do something different?

Is there a common pattern, strategy or framework that successful projects use?  And if so, can we model it and use it in our own projects?

These are the questions I've been asking myself recently as I dive headlong into my new publishing startup. The essential question is this:

How can I avoid the pitfalls of unsuccessful startups and tap into the magic of the successful ones?

Creating Success

What I've compiled here are the fundamental dos and don'ts for bootstrapping a business from scratch.

All of these lessons I learned from the masters of the trade (Michael Masterson, Eric Ries, Seth Godin, Chris Anderson, and Nassim Taleb among others) and applied in my own projects.

What you see here is the distilled wisdom of dozens of heavyweights in the business world, as well as the knowledge I've learned from hundreds of books, courses and personal interactions, whittled down into a no-fluff, practical resource you can apply to your own project.

Most of this advice applies to bootstrappers and creative entrepreneurs - but it also applies to the artist, designer and leader.

The lessons included here are universal and impact all of us who build things from the ground up with our bare hands.

So if that applies to you, definitely bookmark this page for future reading.

Good luck, and enjoy:

2 Things You Should Avoid At All Costs:

What not to do with your business is important: the majority of failures are a result of putting time and energy into the wrong things, and if we know what these things are, we can purposefully avoid them.

The 2 biggest don’ts of creating success in business and life are just that – things you should definitely, at all costs, avoid:

1.  Avoid Re-routingre route to what

Re-routing is spending all your time building a solution…to the wrong problem.

This is one of the most common mistakes beginner-level entrepreneurs make.  But it’s not just a beginner-level mistake – plenty of pro’s make the same mistake when they branch out into a new sector, industry, or genre.

Anytime we try something for the first time, we're liable to miss the mark.

That's why it's essential we constantly reevaluate our position, direction and goals (more on that below).

The Lesson: know what problem you’re fixing and why.

2.  Avoid The John Carter Mistake

John Carter was an epic failure in the box office.

Even when things weren't looking good on set or in test groups, the producers continued to pump cash into the project. By the time they shipped, they needed to make close to $400 million to make money on the project.

With every dollar they pumped into the project, the more unlikely their chance of success.

The Lesson: don’t pump money, time and resources into a project that isn’t working.  A sinking ship is a sinking ship - better to cut losses and find a new way to be successful than drown in pride.

9 Ways to Increase Your Chances of Success (in business and life):

It's essential you avoid the two pitfalls above.

Simply put, if you spend your time re-routing or get sucked into the John Carter Mistake, there's literally no way your startup will make it.

But let's say you can and do avoid these two major pitfalls...then what?

What CAN you do to actively improve your chances of success.*

*Note: success is relative and subjective.  In this case, I’m defining success as creating something people want to (and will) pay money for without your business going under (i.e. making profit so you can grow your business).

The following is a list of the 9 best ways you can increase your chances of success, both in business and in life:

1.  Challenge Everything

Just because things are the way they are doesn't mean they should be that way.

No matter what industry of business, genre of art, or category of book, there is always a way to improve the existing paradigm.

There are better systems, better solutions, and better products waiting to be created.  The question is: are you willing to create them?

"Never accept the status quo – there is always a better way."  - tweet this

Ask yourself:

Is there a way this product or this service can be made better?

Why is this the way it is?  Can it be improved?

Where is their a problem and how can I fix it?  What are the pain points of others?  How do I help them?

Is there something missing that I can fill?

This philosophy (and it is just that - a philosophy for living life) of challenging everything includes challenging your own assumptions and beliefs.

Be relentless. 

Constantly test your assumptions and, if need be, change your beliefs - they might just be holding you back.

2.  Know Your "Why"

Why are you doing what you’re doing?

Why do you want to create this piece of art?

Why do you want to build this business?

Knowing why you do what you do is ESSENTIAL.  At the end of the day, your why is what determines your success because it directly feeds your solution (your what) and your execution (your how).

Why, how, what - this is what Simon Sinek describes as the "Golden Circle" - check out his short, powerful video below on starting with why.

"People don't buy what you do - they buy why you do it." Simon Sinek

If you aren't sure of your why, but you’re building something anyway, you’re probably rerouting.

Know your why - and then start with why.

3.  Hypothesize

No project should start without a hypothesis.

In The Lean Startup, Eric Ries explains businesses through the lens of a scientific experiment – in other words: testable, measurable, and reproducible.

Ries’ startup philosophy revolves around creating a hypothesis for your product or service – if we do X, then Y will happen.

“the goal of a startup is to figure out the right thing to build – the thing customers want and will pay for – as quickly as possible.” The Lean Startup

For example: if I add an email subscription box to the end of every blog post, I will increase my subscription rate by 7%.

Or, if I decrease the price of my product by 5%, gross revenue will increase by 10%.

The point isn't to know if it will work – the point is to have an idea, create a hypothesis for the idea, and then test it.

If it fails, tweak it and try again (email subscription boxes at the top of the blog post, or in the sidebar, or add a popup box to your site, etc.).

Constantly test.  Constantly measure.  Constantly learn.

And always adapt and grow.

4.  Be Willing to Change Strategies

When we hypothesize, we create a question that can be tested and proven right or wrong.

If the solution doesn’t work for a particular product or service, tweak the hypothesis and try again.  This is changing tactics – the small scale engagements we make with customers or inside our business (i.e. changes to how we write our sales copy; changes to visual presentation, etc).

Changes in tactics don’t change the fundamental problem you’re trying to solve – changes in tactics simply mean a shift in how we approach the problem.

However, at some point, we might find that nothing is working for our original hypothesis.  At this point, it’s time to change strategy - or, in Lean Startup terms, pivot.

"Life is too short to build something nobody wants." - Ash Maurya

Below is a video by Ash Maurya, author of Lean Running, who explains how to create products efficiently and effectively, why most startups fail, and how you can avoid making the same mistake:

If you found the video useful, make sure to check out Maurya's amazing, free lean canvas tool here.  It will help you map out an effective, simple business plan.

If you have a hard time filling it out, it probably means you're missing a key piece of the puzzle for your own business.  This will help you avoid creating a product that no one wants.

Pivoting means changing your business or business model.

This could mean changing from a "freemium" model (free content to bring people in; sell them paid premium content later on) to a premium, upfront monthly subscription model; from a company that produces and sells information products, to a company that builds software solutions.

Pivoting is sometimes drastic. 

It can be scary and it’s never easy (it challenges our pride because it means admitting our original ideas were wrong).

But if you know your why, pivoting becomes a lot more bearable.

5.  Expose Yourself to Positive Black Swans

The Black Swan is a term coined by Nassim Taleb in his groundbreaking book of the same name, which focuses on probability, randomness and human rationality.

A Black Swan refers to an event that is unpredictable, but has massive impact in our lives.

The internet, for example, was a positive Black Swan event; now we are a few keystrokes away from almost anybody in the world, increasing connection and freedom throughout the world (this change was unpredictable and completely changed the economic landscape of the 90's and beyond).

The terrorist attacks on 9/11 were a negative Black Swan event - the ramifications of which we still experience every time we have to take our shoes off at the airport.

So while we can’t predict when or what form a Black Swan will take, we can focus on exposing our business and our life to positive Black Swan events (and, likewise, protect against negative Black Swans).  A few ways to do this:

  • Don’t over-invest in any project (see: John Carter Mistake above)
  • Do business in positive Black Swan arenas - things like art/entertainment and lean startups…not things like bonds and risk mitigation services.
  • Accept small loss for major upside – do not sacrifice major upside for small profit.
  • Focus on creating a business that has unlimited upside and limited downside.
  • When in doubt, be the owner not the employee.

Here's a lesson on Black Swans from the movie Grinders with Matt Damon.  It's 30 seconds long - it sums up why playing it safe isn't the way to live life.  Sometimes, you have to take a chance:

Taleb recently published a new book called Anti-Fragility - which explains in more depth all the things that gain from disorder.  A must read for all aspiring entrepreneurs looking to make a dramatic impact (and limit their downside exposure).

6.  Aim Small, Miss Small

In the movie The Patriot, Mel Gibson’s character teaches his son how to shoot.

His advice – aim small, miss small.

Once you know your "why" you should focus on the most specific problem you can fix (every product or service fixes a problem).

The smaller, as in, more particular and precise the problem, the better your chances of hitting your mark (because you know exactly what you’re aiming for).

Shooting from the hip (i.e. seeing what will stick) is usually not the best solution to anything.

Be Specific.

Be precise.

Focused on one problem and one problem only to start – and be relentless about defining that problem and your solution.

7.  Start Local

You do not need a website, a team of coders, or a dozen virtual assistants to get your business off the ground.

You do not need angel investors, the Shark Tank or Donald Trump to pick you.

There is a way to test and validate every product before going full scale, and guess what?  You can usually do this by yourself.

Your job is to figure out how to test your solution in the smallest way possible.

Below is a video by Neville Medhora, a guy who does a crazy amount of business testing (from drop shipping companies and one and one consultation services, to eCourses and digital products).

If this doesn't open your mind to what's possible, I don't know what will (warning: some swearing is involved):


Before you start your LLC, lock down the manufacturing and distribution facilities, and enlist a team of salespeople, maybe it would be more effective for you to create the first product and hustle it by yourself.

Can you sell it on Craigslist? 

Can you sell it on Ebay or Etsy? 

Can you set up a stand outside an event and sell it to real people?

The point is this: you must test and VALIDATE before you start scaling.

Sorry, but if it doesn't work on a small scale, it won’t work on a massive scale (Facebook started out on a single campus, McDonalds on one street corner, and Apple with one product).

8.  Work ON Your Business...

Don’t work in it.

Working in your business is essential, but only in the beginning.

It’s necessary to work inside your business at the start; you need to know how it works so you can develop and refine your processes and systems.  But once you have the systems in place, and a profitable product or service, start hiring others to do your job.

Your goal should be to create a  profitable, organized and systematized business so you can scale.

You really shouldn't be hiring people until you're profitable (there are exceptions to the rule - I'm addressing solopreneurs/bootstrappers in particular here).

Working on your business and not in it is a concept heavily analyzed in The E-Myth Revisited, which explains the success of any startup requires the ability to create systems and processes in order to make your business turnkey.

Here's a video all about creating systems for your business from the author himself:


Creating a business is the only way to attain actual freedom through your creative work.  As long as you're an employee or self-employed (i.e. a freelancer), you're at the beck and call of others.

Freelancing requires you to be on the clock (it might be fun, but you're still tied down).

If you want to create something that improves your quality of life, that increases your flexibility and freedom, be an entrepreneur -  focus on creating a business, one that can grow and scale, even if you’re not there.

This means working on your business and not in it.

9.  Never, Never, Never Quit.

Yes, you might have to forget the project you’re working on, or change your tactics, or even pivot your strategy - but don’t quit on creating.

Never stop doing what you love because it doesn't work on the first try – it rarely if ever will.

"If I fail more than you do, I win." - Seth Godin

Self-determination and freedom are not easily won - it’s a struggle and you will take some hits.

That’s why so many quit or never try to begin with.

But not you.

Have faith, act courageously and keep fighting.

The Moral of the Story

Is to constantly push your own abilities; to learn and grow and improve; to seek out challenges and test yourself.

You don't have to create your empire this weekend - and, in fact, you couldn't even if you wanted to.

But if you start today, in the smallest way possible (just one word on a piece of paper; just one call to a prospect; just one sketch of your design), you begin the process of creating something brilliant.

And in this singular act, no matter how small, you begin building your empire.

So I guess the underlying moral of the story is this:

Never stop creating. Start today.

If you like what you've read and need help starting, finishing and shipping your project, here are a few ways I can help:

1 - Join the Resistance by subscribing to our newsletter here (it's free)

2 - Check out a book I wrote called 2 Days With Seth Godin (PDF version) or on Amazon Kindle that can help you get your book, business, or blog unstuck.

3 - Check out the Cache where I have books, courses, and more - many that are "Pay What You Want" (your contributions help me continue to write, produce, and publish)

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4 comments on “9 Dos and 2 Don'ts for Creating Success in Business (and Life)”

  1. This should be mandatory reading for every new business owner, artist or student. You have taken 9 brilliant topics and condensed them down into a well written and concise article. Great work Tom and it's obvious the hard work you put into it. Thanks for sending it out. I need to ponder a couple of these while I work in the sand down here in the Dominican sun.


  2. Alan - thanks so much for taking the time to read and comment - I know you're swamped. Hopefully you get some time to relax on the beach at least for a little while 🙂