18 Personal Lessons I Learned From 18 Years of Entrepreneurship

Entrepreneurs follow a unique path, and sometimes the life advice we collect from friends, family and the web isn’t quite what we need. Instead, we seek advice that suits our lofty professional goals and crazy lifestyles, and such advice is often difficult to obtain.

I’d be lying if I said I’ve mastered the entrepreneurial lifestyle. However, over 18 years of entrepreneurship, I’ve gathered a few personal tips that make our unique balance a bit easier to attain. Write these down, memorize them, tattoo them onto your arm — regardless of how you choose to remember them, make sure to integrate them into your own work and lifestyle. You’ll be glad you did.

1. Borrow and loan money to friends and family with caution.

Loaning someone money to kickstart a business isn’t quite as simple as the time you covered their drinks on a night out. The same goes for borrowing money; the transaction shouldn’t be taken lightly. The strain from owing someone money, or waiting to get it back, can ruin a relationship, no matter how strong it was to begin with. Only do it when you really have to.

2. Every married business owner has two spouses — their business is one of them.

You spend a lot of time thinking about your business. You center many of your goals around it, and you spend a lot of time with it. You’re practically married to your business. But don’t forget that even when your company needs a lot of attention, so does your actual spouse — and unlike a business, your actual spouse will eventually run out of patience.

3. Your kids deserve your attention.

No matter how busy you get with your business, make sure to set aside time for your kids. When you think you’ve reserved enough time for them, reserve even more. The memories you’ll make with your children are even more valuable than anything you could do with your company.

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4. College is cool for some, but hard work and passion trump all.

Most people today grow up with the expectation that they’ll go to college. While it’s a fun experience and worthwhile investment for some, it simply isn’t necessary for others. Think about your long-term goals. If you can meet them with hard work and passion alone, you may not need to take out those student loans.

5. Work out to decompress.

You don’t have to buy a “Fitness = Life” t-shirt or splurge on an expensive gym membership to reap the benefits of exercise. An early morning jog or twice-weekly fitness class is enough to boost those endorphins, work out physical soreness and stress and even allow you a better night’s sleep. Some people even say that working out in the morning allows them to be more productive throughout the day.

6. Take a deep breath. You need it.

Step back and take a deep breath when things get stressful. Close your eyes, and notice the way your chest feels when it fills with oxygen, then feel the air rushing out of your nose when you exhale. You can even download an app to remind you to breathe throughout the day. It’s important to separate yourself from the havoc now and then with a deep breath.

7. “A bird in the hand is worth two in the bush” is probably true.

The grass is always greener on the other side. All that glitters is not gold. No matter how you phrase it, the central concept is the same — what you have is normally just as valuable, if not more so, than what you could have. Practice appreciating the things you already enjoy, as you’ll otherwise only appreciate them after they’re gone.

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8. Loyalty is important, and so is equal contribution.

Loyalty manifests itself between people who share a common feeling or goal. Likewise, people feel more compelled to contribute to a cause when they share a goal with their peers. Never take one without the other; loyalty without equal contribution is complacency in disguise, and contribution without loyalty will cause you to lose sight of your goals. The two elements go together like peanut butter and jelly; give both, and you’ll get both.

9. Handouts are never really free.

Favors are done to build a relationship or earn an IOU. Don’t get me wrong, some people genuinely want to help you and your business, but never assume that you don’t need to give them something in return.

10. Your work ethic defines you.

When people hear your name, it should remind them of your outstanding work ethic. People admire hard work, and they will respect your end product more if they know how much elbow grease you’ve put into it.

11. Work smart and hard — but smart first.

Bill Gates once said, “I choose a lazy person to do a hard job because a lazy person will find an easy way to do it.” This isn’t permission to be lazy — see tip 10 — but there’s something to be said for those who seek smart solutions to problems before taking the hard route. Always check for a clever way to finish a project before taking the road most traveled.

12. Be inquisitive.

Speak up, ask questions, and seek solutions from outside the box. Be an independent thinker. You’ll never be revolutionary if you do the same thing everyone else does.

13. Be optimistic, but don’t lie to yourself.

There’s a fine line between optimism and an unrealistic hope for the future. Don’t lie to yourself about where you or your business are going. Plan for the worst and hope for the best.

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14. Having an ego isn’t a bad thing — having a bad ego is a bad thing.

Confidence, creativity and a robust work ethic will build people’s trust in you. Cockiness, a snobby attitude and being unwilling to listen to others’ ideas will quickly dissolve that trust.

15. If you change jobs, get an exit, or experience a big setback, take a little bit of time off.

Major change requires major adjustment. Whether you’re facing a job change, the sale of your company, or an entrepreneurial setback, take some time off to breathe. You need to gain some perspective before moving forward.

16. Follow through with your promises.

Do what you say you’re going to do. Don’t make excuses; just do it. Flaking out is the fastest way to ruin a professional relationship.

17. Be good to people, and your imperfections will be less visible.

People are far less judgmental toward those they like. Be good to those around you, and people will begin to notice the best in you, not the worst.

18. Don’t lie, face the music and grow.

Sometimes the toughest things you’ll go through are the ones that make you a better person in the end. Face your challenges head-on, and when things get rough, focus on how much stronger you’ll be after the fact.
None of us is perfect. In fact, most of us are very flawed. The entrepreneur’s path is a road less traveled, a rocky one full of pitfalls and mountains to climb. But with the right tools and a proper mindset, you’ll grow right into the role and feel comfortable filling it.

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