The startup world has glorified the “fail fast, fail often” ethos to the point that many young entrepreneurs still think that a grueling trial by fire is the only way to be legitimate. Not only that, but they view repeated failures as a linear narrative rather than an exponential process of learning and evolving.
The problem is that when you become laser-focused on rushing your next big idea to market, you’re forced to spend a lot of time fixing your mistakes. You become so bogged down that you never have time to look at the bigger picture for your business or your life. You risk missing out on what I consider the true benefits of entrepreneurship: doing what you love, doing it with people you love, having time to pursue other passions, making an impact and being well-compensated.
The unromantic truth is that lifelong entrepreneurs are actually much more risk-averse than most people think. They’re masters at handling risk because when you have 10 employees whose families depend on you, you can’t move too fast and you can’t break too many things.
That’s not to say seasoned entrepreneurs never fail. They do try things that don’t work out, but they take the lessons from those experiences and use them to make exponential leaps forward. They understand that “fail fast, fail often” is not a road map—it’s a recipe for disaster and burnout.
When my brother and I started our own company, we didn’t try to do everything ourselves. I kept the components of the engineering role I liked and hired people to do the things I didn’t. Ultimately, we grew that company to more than 200 people.
I like to tell this story because it offers an alternative narrative to the idea that you must shoulder everything yourself and slog through one failure after another. That mentality is unsustainable and robs you of the joys of entrepreneurship.
Here’s a healthier way to build a successful business:
1. Create a life plan.
The first and most important step is figuring out what you want your life to look like. One helpful exercise is to imagine attending your own funeral. Who is there, and what are they saying about you?
This exercise can be really illuminating because it shows you what you value most and how you’d like your life to look. From there, you can create a wish list for the next 10 years. What do you want for your career and relationships? What do you want your finances to look like? Once you have your 10-year personal targets in mind, break those down into smaller goals for the next one to five years.
2. Integrate your life plan with your business plan.
To realize your 10-year life plan, it’s important to understand how your vision for your life integrates with the practical realities of your business. If your life plan revolves around freedom (“I’m going to work 25 days a year and have a $300 million business”), that’s going to be difficult to achieve. You must understand how the 10-year targets for your company align with your personal targets.
When you become laser-focused on rushing your next big idea to market, you’re forced to spend a lot of time fixing your mistakes. You become so bogged down that you never have time to look at the bigger picture for your business or your life.
To do this, you must get crystal clear on your unique value proposition, the problems you need to solve as a company and your marketing strategy for the next one to three years. Only then will you be able to bring your business realities and personal goals into alignment.
3. Obsess over delegation.
Leading from a higher level starts with self-awareness: You should understand your own strengths, weaknesses, likes and dislikes. When you start focusing on what you love and what you’re good at, you’ll always be doing your best work and you’ll be able to do more of it.
To put this into action, you can draw a chart with four quadrants. The top left quadrant is for things you absolutely love and are great at. The top right quadrant is for things you like and are good at. The bottom left is for things that you are good at but don’t enjoy doing. And the bottom right is for things you don’t like and aren’t good at.
Then make a list of all the tasks you personally handle and categorize these activities into those four quadrants. You should look to delegate, automate or eliminate anything that falls in the bottom two quadrants.
4. Surround yourself with people you can enroll in your 10-year vision.
Once you know how you should be spending your time, you can use your quadrant setup to prioritize your hiring. The goal is to find people whose top quadrant is a close match for your bottom quadrants. When you find people whose strengths and desires are the inverse of yours, you’ll be able to remove the tasks that sap your energy and pursue the things that energize you. Finding people to whom you can delegate will also give you the bandwidth to step back and see the bigger picture.
By being honest about what you’re good at and how you want to spend your life, you’ll be able to move forward with clarity. (You’ll also be less likely to suffer repeated failures from a lack of foresight.) You’ll be able to put a team in place to achieve your goals so you can spend less time breaking things and more time building things.
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