The 10 Most Gratifying Things I Experience as an Entrepreneur

Nate McCallister đź’ˇ
4 min readOct 4, 2022
Highly gratifying…

Entrepreneurship has been one of the great joys of my life.

In a world where nearly 50% of people report dissatisfaction with their jobs, I’m extremely thankful that I enjoy what I do.

Some things stand out as abnormally gratifying, though.

Here are 10 of them.

Note: I do not include the biggest thing, which is the freedom of time and focus. The ability to spend time with my friends and family when and how I want. For this article, I’m focused on business-specific things, not the corny and obvious :)

Let me know which things you find most gratifying in the comments.

#1 When you legally deduct cool stuff from your taxes

Emphasis on “legally.”

Although I have no problem paying my fair share, the tax laws are built for a reason, and we have every right to leverage them.

The IRS wants us to invest our money in certain ways, and they reward us for it if we have the sense to take advantage of the opportunities available.

As long as the purpose of the expense is to produce more income, it can be deductible. — Rich Dad Advisors: Tax Free Wealth: How to Build Massive Wealth by Permanently Lowering Your Taxes

Yes, sometimes that means taking clients out for fancy dinners to make new business deals and generate more revenue. Sometimes it means buying a fancy new computer that will be used for business, but you wanted it anyway.

#2 When you’ve trained someone, and they start doing high-value work on their own

Outsourcing and delegation are amazing but not easy. Anyone who has ever tried to outsource a difficult task knows that it’s not as simple as saying, “Welp, here ya go! Get after it.”

It takes a tremendous commitment to delegate tasks effectively, but the reward is even greater.

As I write this post on Medium (which I do mostly for fun rather than for generating any serious income), I have a new team member who is working on building white hat backlinks for my websites. This was something that took a ton of my time, and I dreaded doing it. But, it is a high-value task that needs to be done in order to grow my traffic.

It took several weeks to teach but is now almost entirely done by my new partner.

#3 When a new piece of content gets organic traffic

This is especially true if you’ve ever paid for traffic and understand how valuable it can be.

When you start to see a surge of “free” (not really free, of course, but I’ll save that for another post) traffic from a piece of content you worked hard on, the endorphin taps open wide.

Especially since most content doesn’t perform as well as we hope it will.

#5 When you find a deep work state and complete a project you didn’t think you could

Deep work is one of the most glorious feelings for entrepreneurs, especially creative types who need it to get quality work done.

This flow state of work is difficult to get into, but when you do, time melts away like butter, and you can create amazing things with little friction.

#6 When people tell you that you’ve helped them

I don’t think people fully appreciate how much it means to hear someone say something like, “Hey, I really liked (that thing you did).” Or, “I tried (that thing you talked about), and it helped me so much!”

These seemingly ordinary comments are like shots of adrenaline.

Especially when you have to battle your own self-doubts and criticisms.

#7 When you find new software that produces results

I prefer to keep my businesses as small as possible.

If I can find new software that helps me grow without hiring and training new people, it’s euphoric.

As a bonus, I love when I get to introduce my readers and followers to the new tools that I’ve found. You feel really cool when you’ve found something that other people will enjoy.

#8 When you break even on a risky investment

The closest I ever get to gambling is investing money in my businesses on things that I am not positive will pay off.

When they do, oh mama…

#9 When you’re asked to speak at an event

It’s a serious ego boost to find out that someone thinks highly enough of you that they want YOU to teach people who are paying them.

Even if I can’t attend an event, I always make it clear that I am extremely honored to have been asked.

#10 When subscription payments start to add up

Entrepreneurs love that “passive income.” I think the phrase is misleading since we usually just did the work in the past and got paid for it later, but I get it. The feeling of nurturing steady income streams is glorious.

What are some things that you love about entrepreneurship? Let me know in the comments!

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Nate McCallister đź’ˇ

I over analyze topics in the internet business, productivity, fitness, nutrition and self development space. I share my findings here đź‘Ť