4 Entrepreneurial Lessons I’ve Learned Over the Years

By Saturday, October 18, 2014 2 Permalink 1

entrepreneurial lessons learned

I’ve launched many projects. Each with their own set of challenges. Some have failed, which means learning opportunities. For today (since it’s the 100th post), I want to highlight some entrepreneurial lessons I’ve learned over the years.

1. Be extremely selective when adding people to your team.

Think of every project you start as your baby. You wouldn’t leave your child with just anyone, right? It has to be the same way with your business — if even just a small part of it. I’ve learned that finding help and finding dependable people are two different things. For the projects that have succeeded, I’ve had team members that contributed regularly without being asked. They treated my baby like it was their own, and they were there even when I didn’t need them. They bought into my vision and it showed (more on this later).

For projects that didn’t do so well, I’ve had to chase people or take over their workload because they weren’t delivering. In fact, I had to work harder because of them, which meant I wasn’t at my best for the things I was best at. Also, let’s not forget that anyone you bring onboard has the ability to tank your brand reputation. When you’re trying to get your business off the ground, there’s no space for that.

2. Free is good, but it makes you a lower priority.

Getting someone to do free work is great. It saves you money and time. The problem is that when someone does free work for you, you automatically move down their priority list. Everyone has that graphic designer, resume reviewer, or other skilled person that says “Sure, I’ll help you out for free.” Things are awesome at first, but then 2, 3, 6 weeks later, you still haven’t gotten that thing you asked for and there’s nothing you can do about it. In fact, you’ve probably been that person at some point (I know I have).

Even if you don’t have a big budget, you should always offer to pay something. Make the time worth their while. Best case, they turn down your money. Worst case, they accept it. The good faith gesture eliminates concerns about being used or taken advantage of. You never want someone to feel that way (I’ve felt it).

Other note: If they say no to you altogether, this is a good thing. Better that than finding out weeks or months later!

3. Doing things that only bring you money will only bring you chores.

If you’re starting a project or business, it’s best to start something you’ll enjoy long term. Something you’re passionate about. When you start a project with the sole goal of making money, it’ll eventually feel like a chore. Nobody likes those. And even worse, your work quality will reflect your growing disdain. I know I’ve embarked on a few things because I thought they’d have me laughing my way to the bank. Guess what?

It wasn’t funny at all.

4. Vision is everything.

Related to the previous point, you need to have a vision for whatever projects you start. It can include an end-goal and check points to hit along the way. This will inform your strategy and, more importantly, what you say yes and no to. One of my biggest struggles has been wandering all over the place or getting easily distracted because something “looks cool,” or saying yes to something that becomes a value-addless timesuck. Say yes to things that get you closer to your goals. Say no to things that don’t. Sounds obvious, but…well, I’m sure you’ve been there.

Another thing: your vision should not be dependent on others. Goals like “to have a popular blog” or “be known on Twitter” are crap. You’re essentially putting your success in the hands of others, which is the antithesis of freedom. Also, these types of goals are devoid of a sustainable and actionable Why. Here’s an example and exercise to demonstrate what I mean:

I want to have a popular blog.


So I can get free things from companies.


So…I…can…um…I don’t know. Leave me alone!

You’ll learn a lot about yourself when you try this. Maybe even that some of your goals are more superficial than you thought. Just remember that superficial doesn’t last.

What lessons have you learned? What would you add to the points above? 


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