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Best Side Jobs that Enhance Your Entrepreneurial Skills FAST

If you’re trying to make it in your life as an entrepreneur, you have probably already been faced with this classic entrepreneurial dilemma…

How do you pay your bills while you build your own business?

I’ve been working on building my own businesses for most of my life. And yet, I’ve also held down several interesting (and helpful) jobs during those years.

And the truth is that choosing the right type of side job could have a HUGE impact on how successful you are with your side-hustles/business.

If you want to succeed as an entrepreneur, it is important to understand that your side job can be a huge asset!

Some people quit their jobs cold-turkey and run out of savings before learning how to make their business profitable.

Some people get discouraged when their day job stresses them out too much, and they end up giving up their entrepreneurial dreams and caving-in under the pressure.

But the truth is that it takes time, effort, and determination to succeed as an entrepreneur… and the right side-job can absolutely help to push you over that threshold of success.

But what side jobs are the best?

In this post, I’m going to tell you exactly which jobs are the best for building entrepreneurial skills.

I’m also going to share the number one secret-ingredient to success that my side jobs taught me over the years!

Let’s get started.

Why a Side Job Will Do You Good

benefits of a side job

If you've been drinking too much of the fake guru's Kool-Aid, the idea of "Jobs for Entrepreneurs" sounds like an oxymoron...

It may not compute...

But for Melanie and I, it took holding down jobs for many years to support our entrepreneurial venture...

We had to pay for rent, food, car insurance, credit card bills, student loan payments, etc...

Plus there were expenses like hosting, email providers, keyword tools, etc...

The fake gurus make it sound like you are 1 funnel away and it's easy to build in an afternoon...

The truth is that we were 1 entire business away and it took 4 years to build...

If you go 'all in' on your business too early, you'll run out of cashflow for LIFE before your business can stand on it's own two feet.

Tried this a few times, and it ALWAYS failed miserably...

This is why I had to move back in with my parents at 30 with my tail between my legs.

But the time we got it right...

The business we are still growing to this day (9 years later)

That has now generated millions of dollars in revenue...

It took 4 years of nights, weekends and 40+ hour weeks of brutally confusing effort.

And these 40+ hours were on top of the 40 hours we put in at our full time jobs so we could support the business in growing.

Here's the key, tho...

The jobs we chose were VERY specifically selected for a few key reasons...

And these jobs actually helped us both grow to be more valuable and to gain powerful insights that helped our side business grow faster.

There are basically two different reasons to get a side job… money, and experience.

If you need to pay bills while you build your business, then you are going to need to get a job anyway. At the very least, you’ll need one to support yourself until you start earning enough to make it on your own with your business.

But getting a side job can also be worth it from an experience perspective.

Almost every side job is going to teach you valuable lessons that will help you on your journey as an entrepreneur (though some will certainly teach you more than others).

Great Discoveries from Having a Side Job

My wife, who has done very well for herself in the meditation niche, learned while managing a metaphysics store years ago that the personal contact she had with customers in a retail setting absolutely set her up for success with her own business.

She was not only growing her own meditation business… she was also literally immersing herself into her target demographic at her day job as well!

She learned so much from this experience, and it helped her to succeed in a truly massive way!

Syncing up her business and side-job like that allowed her to double-down on what she loved to do… and as a result, her business prospered due to all of the knowledge and experience she was bringing back to it!

My Journey From Side Job to Full-Time Entrepreneur

journey to a successful business

Many people think that I just ‘jumped into’ this life of digital marketing I live right now. But nothing could be further from the truth.

I’ve had a lot of different jobs over the years that have taught me valuable lessons, and I needed these lessons to succeed.

In fact, my wife and I had to grind for 4 years while STILL working full time jobs to get our online digital marketing businesses up and running to the point where they would support us.

For 4 years, we worked every weekend, almost every night, and got up early every day at 4 AM.

I even created marketing jobs for myself with local businesses.

I’ve also worked a number of side jobs over the years that have contributed to helping me get where I am today.

3 Best Side Jobs That Build Skills of an Entrepreneur

best side jobs

Every job will teach you lessons about business. But there are some that are still simply better than others.

So let’s talk about the most helpful types of side jobs to get if your goal is to one day become a master entrepreneur.

1. Sales

Become a master salesman.

Becoming a master salesman is probably the number-one best skill that you can practice through a side-job.

I’ve sold web hosting, I’ve sold cars, I’ve sold advertising, etc. And all of these experiences have helped to prepare me for my role as an entrepreneur.

If you want to do business, you must learn to sell.

Point. Blank. Period.

2. Customer Support

Connect with your audience and solve problems.

Customer support is another one of those crucial types of skills that your experience at a side-job can teach you.

If you never learn how to deal with customers effectively, you are going to suffer tremendously when the time comes to do the same thing for your own business.

Make no mistake. Even the most entry-level customer service position at a side job can teach you A LOT about how to build trust and rapport with customers.

3. Small Business that Involves Digital Marketing Skills

Learn, execute, master the skills.

Digital marketing is the new frontier for business.

So if you want to succeed as an entrepreneur in the future, you must learn about these skills and develop them.

If you can get yourself involved in a small business and take on a position that requires you to do some basic digital marketing, you will learn a lot of essentials that you will doubtlessly use in your business later on.

I did this when I sold cars. I designed listings, took photos, wrote copy, etc. I also did this for other businesses over the years.

And these experiences did SO MUCH to prepare me for the destiny that I have achieved for myself today!


There are definitely a few key skills that you should be trying to develop as you work toward starting your own online business.

Of course, every business is a little bit different. But nowadays, you pretty much NEED to hone these skills if you want to come out on top.

If you can find a side job that will give you experience in one or more of these fields, seriously consider going to work with that company!

A little bit of experience in any one of these categories will go a long, long way toward making you a greater, more accomplished success!

WordPress Website Development

WordPress crushes it with website development. There simply isn’t a better alternative for the money!

And the more you know about it, the better off you will be!

Affiliate Marketing

Affiliate marketing is one of the best ways to build a modern business from the ground up. Even if you do other things with your business, you can still earn awesome cash with affiliate marketing.

But make no mistake… just because affiliate marketing works for some people doesn’t mean that it’s easy!

Work hard to develop this skill, and don’t give up. In the future, it can really pay off!

Social Media Marketing


Like it or not, social media is here to stay. And while some platforms may not work as well for marketing different types of businesses, it is also important to point out that knowing how to use social media for your business the right way is HUGE.

So if you can gain experience in this area, you will reap a lot of rewards from it.

Content Marketing

Content marketing usually takes the form of either blog posts, podcasts, or YouTube videos.

Creating valuable, optimized content is one of the best ways to drive real, organic traffic to your website.

Gaining experience in this area will do a lot to prepare you for the process of growing organic traffic for your own business.


Copywriting is such a vital part of the modern-day business that you really can’t survive without it.

The more experience you have in this area, the better!

As an entrepreneur, you are likely going to have to start out writing your own web content, emails, sales copy, Google advertisements, funnel content, etc.

So if you really want to hit the ground running, find a way to level up this skill through your side job!

Content Writing

Content writing is very similar to content marketing, and usually involves writing website copy, blog posts, white papers, and sales papers.

This is a skill that you will use to bring value to your customers. But it is also a skill that you will use to drive organic search results to your website.

Content writing is also a trust-building skill… so it is super-important to master it and learn how to use it in your own business!

SEO Skills

Search Engine Optimization is very, very crucial to winning with an online business!

If you can gain some experience in this category and level up your skills, you will be ‘Miles’ ahead of the curve!

(See what I did there?!!)

Graphic Design

Graphic design is a skill that will help you with branding, marketing, website design, etc.

We live in a very visual world, and the better you are at graphic design, the better your chances will be of gaining the attention of your target demographic.

Other Technical Skills

There are obviously other technical skills that can help you to become a better entrepreneur… and the more closely related to your business they are, the better!

When I sold cars, I was in charge of taking pictures of them and putting together the online listings.

This gave me some photographic experience that, today, helps me with photography work on my website.

Sure, I can hire a professional photographer now… but that’s beside the point. The point is that I have some technical experience in that department now that helps me in making relevant, helpful decisions about my business TODAY.

And that is knowledge that I will always have. It is a huge asset, even if I don’t use it every single day!


Starting your own business is an awesome dream, and I wish that more people took it more seriously.

It is not easy… but firing your boss and living life on your own terms is 100% worth it!

With that being said, getting the right work experience along the way can do a lot to help you find success later on in your own endeavors.

So choose a side job that will give you the kinds of skills that will help you later on. Be intentional about what you do with your time, and use every possible moment to help yourself succeed!

If you have any questions, please drop them in the comments. Where are you in this journey right now? Are you thinking of starting your own business? Let me know and let’s talk about it!