How To Build A Rock-Solid Entrepreneur Mindset And Break Through Plateaus

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Building an important company over time has a lot to do with product, capital, team and market.

It has more to do, however, with what you (the entrepreneur) tell yourself every day during those “internal conversations” that play out in your head.

Entrepreneur psychology is the most under-appreciated, yet most important part of building a company. It rarely gets any attention because it’s not “sexy”. But man is it important.

Everyone talks about startups being akin to roller coaster rides. There are high highs and low lows. The highs are easy to deal with — you celebrate with your team, share the victories with your friends and partner and maybe even down a few beers that night.

What’s harder to deal with are the (seemingly constant) lows — when things don’t work out as you expect them to. Examples include having an important employee resign, a potential investor pulling a term sheet at the last minute, a competitor winning a big partnership deal and employees passing away.

All of these have happened to me at some point in the last 10 years. And the only way through all the shit is to make sure you talk to yourself every day — but in the right way. Not out loud, of course, but in your head.

There are also certain ways you can look at problems to quickly figure out if they’re potential “company killers” or if they’re just bumps along the way.

As a CEO, you need to find constant inspiration and rationale to move forward. That’s what I’m hoping to give you in this post.

Here are some “no bullshit” ways to manage your psychology as a CEO. Everything here comes from my direct experience over the last decade or so building Bigcommerce ($100M+ annual revenue, $10B in orders, $250M raised from investors) and a few other companies.

1. Use best/worst/probable analysis when weighing decisions

Most things we fear never materialize, but we spend so much time stressing over the “what ifs”. An alternate approach is to look at decisions and problems rationally by creating a best/worst/probable case analysis.

It’s easy to do — create a spreadsheet with the following columns:

  • Outcome
  • Chance (%)
  • Stop
  • Start
  • Keep Doing

… then fill in the spreadsheet with 3 outcomes:

  1. Best outcome
  2. Worst outcome
  3. Probable outcome

Chance (%) is the chance of that outcome happening. It’s a percentage from 1 to 100. In the “stop” column, list the things you’d stop doing if that outcome came to fruition. In the “start” column, list things you’d start doing if that outcome came to fruition. In the “Keep Doing” column, list things you’d keep doing if that outcome came to fruition.

Pretty simple stuff, but writing down each possible outcome and looking at things objectively and rationally can help get the negative, fearful thoughts out of your head extremely quickly, especially when you realize the chance of the worst outcome actually happening is probably tiny.

2. Focus like crazy to make meaningful progress

Progress beats the crap out of fear. Every. Single. Time.

If you feel like shit, commit to spending the next 24 or 48 hours working your ass off to make meaningful progress on something that’s important to you — and it does NOT have to be about your business.

You could run 10 miles each day, spend more time with your partner, design a new product, write a 10,000 word blog post. Whatever it is, make sure the effort is rewarded with a legitimate feeling of progress in some area of your professional or personal life.

Feeling like things aren’t moving as quickly as they should be is the entrepreneur’s curse. You always want things to move faster and it’s easy to get frustrated when they don’t.

3. Know when to step away

Some days you’ll just feel down. It happens to everyone. On those days, don’t go into the office. Cancel your meetings. Spend time alone and do whatever takes your mind off things. Read, write, exercise, play video games. It doesn’t matter.

One big key to maturing as an entrepreneur is to know when you’re just not up to working as you normally would. It might be one day every month or one day every year. But tune in to your thoughts and feelings and don’t fight them.When you’re forcing yourself to work, it’s time to do the opposite.

4. Talk to someone and get advice

As an entrepreneur it’s normal to think you’re the only person who doesn’t know how to solve a problem. But most problems have already been solved by someone else. Instead of beating yourself up for not knowing the answer, talk to someone — ideally a mentor or coach, but if you don’t have one, post on Quora or

Don’t ever be embarrassed to share your problems and ask for help. The best entrepreneurs are the most vulnerable and the most opening to learning and listening to others.

5. Ignore your competition

Your closest competitor just raise $100M. Or they went public. Or they won a big customer. Or they hired a smart executive. Who cares?

Spending too much time thinking about your competitors will run you into the ground. Instead, dial up the time you spend with your customers. If you’re not spending any time with them, now’s a great time to start.

Just email a few and ask them to catch up for a chat. Ask about their business, how they use your product and what you can do to make it better. The main thing you’ll get out of this is real, authentic feedback from paying customers who LOVE what you do. And that positivity will rub off on you and how you feel. Trust me.

6. Watch Tony Robbins videos on Youtube

He’s the master of human psychology, plain and simple. Just go to Youtube, search for “Tony Robbins” and choose a few videos. After an hour you’ll feel like a different person and will get more clarity and a better perspective on what’s important and your current situation.

7. Compare your life today versus 5 years ago

Another easy one. Write down 5–10 things you have today that you didn’t have 5 years ago. This will bring about feelings of gratitude, which will help release dopamine — the “happy chemical” in your brain.

When you write this list, don’t list “stuff”. Write down things about your business, your family (wife/husband, kids), places you wanted to visit that you’ve been to, people you’ve helped, book and people that have changed your life, etc.

8. Realize it takes 7–10 years to make anything truly great

If you’re a few years in, you’re just getting started. 98% of big, important companies took at LEAST 7–10 years to make their first mark on the world.Building an enduring company is a marathon not a sprint. Step back and put this into perspective whenever short term problems are clouding your long-term view.

9. Go to your vice regularly

What’s the one thing you do that excites the hell out of you? It should take100% of your focus and make you feel amazing when you’re done.

It could be exercise, sex, drawing, painting, public speaking, helping someone, volunteering, video games or cooking.

Whatever it is, do it regularly to top up your dopamine levels. If you don’t have a (healthy, safe) vice, spend some time to find one. Try a lot of new things and keep the ones that make you come alive.

What’s the worst thing that can happen?

Suppose your company fails. What’s really the worst thing that can happen? You have to start again? So what. Your lifestyle takes a bit of a hit? So what. Your pride gets crushed? So what. You have to tell investors you’ve lost their money? That’s hard to do, but they’ve baked your small chance of success into their models.

The odds of everything falling apart are so small that most times it’s not even worth considering — and that’s from someone whose been so close to the wheels falling off dozens of times in the last decade.

You might come close, but the wheels rarely, if ever, fall off.

The next time you feel down/upset/angry/frustrated/like shit, step back, be aware of how you feel and do whatever it takes to manage your own psychology — because in the end that’s really all that matters.


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