I want to ask the hard questions for business owners, and anybody who is or wants to become an entrepreneur should think deeply about these.
What are your personal goals? Do you want to earn more? Work less? Both? Do exciting things? Change the world? Or just explore things that you find interesting while making some money?
What are you happiest doing with your time? What activities bring you the most joy? How does this split up into buckets between work, family, friends, and hobbies?
Where do you want to be five years from now? More specifically, what does the perfect week look like for you? Lay out how you want to spend your time, and how much of that is spent working, playing, or socializing. For me, on Monday I want to work all day to kick off the week. Tuesday through Friday I want to work until noon and then either go golf or spend time with my kids, and on the weekends I don’t want to work at all while I hang out with friends or travel.
As an extension, what does that work look like for you in five years? In my world a lot of my time working is simply fielding emails that don’t require action from me–I watch business happen without my involvement. My goal is to grow to make $25K a month without doing much, and that allows me to do more podcasting and teaching.
What are your partner’s greatest strengths and weaknesses? What are they good at and what do they suck at? Do you feel they have the skill set to take you to the next level to accomplish your goals? Do you have the right equity structure to grow your business and feel good about who gets what?
Similarly, what does your partner say your strengths and weaknesses are? What do you do well? How do you add value to the company? Where do you drop the ball?
What is in your 80/20? What 20% of activities generate 80% of your profitability? If you don’t know, I challenge you to deeply analyze and reflect and find your wheelhouse, and then focus on it. For me, that’s structuring new deals, bringing on new equity partners, and making key hires.
Let’s say your phone rings, it’s either a customer or an employee calling. What are the common questions they’re probably calling about? What do they need help with? And how can you delegate these decisions or empower your employees to make decisions so that you aren’t the bottleneck in the business? How can you set your business up to minimize the amount of activity that relies on you?
What is keeping you up at night? What are you stressed about? Some things are minor and can be handled, like a certain job, employee, or customer. But there are bigger-picture stressors too, like your marriage, raising kids, and lifestyle creep. A lot of our stress boils down to money, people, and health.
Think through the path to your goals. Let’s say your goal is to have $5M in the bank in investments, what’s the least risky path for you to achieve that goal? What are the key tasks and milestones to get you there? And similarly, what are the most important things you’ve done for your company in the past year? What key hires, key sales, or key deliverables have you executed? What processes and relationships have you built that will make things easier down the road?
What are your personal goals? What have you been neglecting recently that could get you closer to these goals? What have you been ignoring and procrastinating? And how can you achieve these goals alongside your professional goals?
Take a long time to think about all of these that apply to you. Go through this practice two or even three times to fully consider it, and do this every year to watch as things change. This will make you a much more effective entrepreneur as you have a clear, rational take on all the things impacting your life and your business.
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