Transitioning to Entrepreneurship From a Career

Transitioning to Entrepreneurship From a Career

First things first, don’t quit your job.

If you’re thinking of transitioning into a career of entrepreneurship, it can be really hard to find any concrete pieces of advice. But, there are numerous videos, interviews, articles telling you a few things:

  1. Entrepreneurship takes hard work.
  2. Entrepreneurship is stressful.
  3. Entrepreneurship is not for everyone.
  4. Entrepreneurship is risky.

Cool. You’re comfortable with that. Now what? How do you actually get started, and what does that look like?

First, let’s break down the main misconceptions.

Misconception #1: Entrepreneurship = Immediate Wealth

If you’re struggling to pay rent, or worried about a sudden medical bill, trying to start your own company is not a solution, and quitting a job with that level of importance to your life could put you in a really dangerous situation.

Misconception #2: Entrepreneurship = Overnight Success

Every story of a successful company or entrepreneur took years, but the years it took to figure stuff out are boring, so nobody talks about them. It takes time. That’s why you don’t start by quitting anything, and instead by spending a little extra free time experimenting.

There are far too many stories about successful entrepreneurs living out of their mom’s basement, being on the brink of losing their home, maxing out 5 credit cards to pay their employees, etc. Those are 1 in a million, and they get all the media coverage because they’re much more exciting and scary than the story of someone who did it slowly, intelligently, and safely.

Misconception #3: Entrepreneurship = Infinite Possibilities

While there are a handful of different ways to build a business, some are more realistic than others.

“Venture-Backed” Business

These are BY FAR the least common, the least accessible, and the most unrealistic. Venture capital investment is for the already highly-educated, well-off, men and women that want to make even more money than their lucrative tech job pays. Don’t aim to be invested in. It’s unrealistic for 99.999% of the world.

Service Businesses

For example, a marketing agency, a landscaping group, or even a hotdog stand. Whatever your business, you sell a service to others who need it. These are extremely realistic to build because you create revenue from the start, unlike a “product” business. In fact, many service business owners start as freelancers. You start on your own, bring others on board over time, and end up with an agency.

Product Businesses

This is the category most “startups” fall under. You build a product to solve a problem, and people or businesses buy it from you to solve that problem for themselves. You could be selling a backpack you created for students to hurt their spines less, developing an application to help restaurants take reservations, or building a supercomputer that fortune 100 companies need to manage high-level logistics. These product-focused companies can be very hard to build, as you have to build the product before you can sell it. That’s where the risk comes in. You might build something that doesn’t work, or most often, something nobody wants and nobody will buy. These types of businesses aren’t impossible but are a bit harder than the rest, riskier, and take a whole lot more time to build.

Freelancing Business

This is the most realistic, and often how many super-successful entrepreneurs get started. You could do freelance design for individuals that want to create logos for their businesses. You could do freelance marketing, and help business owners or individuals run ads on their initiatives. You could do freelance resume writing, or copywriting to help others create great language for their projects. Regardless, you’re working on a client basis, so you find individuals or businesses to do work for when they need it. The income is rarely consistent, and it helps to have a network to start, but there’s almost no barrier to entry.

Everything Else

There are literally infinite possibilities. Just to show some, check out Michael Essek’s blog on art business, Peter Askew’s blog on businesses based on domain names, Bobby Kania’s blog on blogging and SEO-based businesses, and my blog/live stream where I conduct experiments in entrepreneurship with people like them. :)

How to Get Started as an Entrepreneur

So, let’s talk about how to actually get started with all of this. We’ll use a couple of examples:

Example 1 - Photography

As part of my series on entrepreneurship, I bought a camera. I was interested in taking pictures, and I wanted to be able to film nice videos for my internet show, so I saved up a few hundred bucks and grabbed the cheapest DSLR package I could find. Since I was editing pictures and videos, I grabbed a couple Adobe products. Overall, I probably spent $800.00.

To see if I could get paid for photography, I asked a few of my friends in the business how to get started. They said events were a good place to start. Without any prior experience, I checked Eventbrite for local events, found a luncheon in a couple weeks, and emailed the host. I said something to the effect of: “Hey, I’m just getting started, but this looks like a fun event and I was wondering if you needed a photographer to take pictures?”

The next morning I got a response. It was a yes, and in two weeks, I came with my camera and took some very poor photos and videos of the event. The settings on my camera were wrong, everything was grainy, and I didn’t take advantage of lighting correctly. But I got paid $200.00, and I had a few good photos to put on a portfolio online.

I didn’t take it further, but that was all it took to get started. A weekend. I sent out one email, but you could send hundreds. You could spend a few hours with your camera before jumping into an event gig. From there, you work hard, slowly raise your pricing from $40/hour to $150/hour, and once you’re able to sustain yourself fully, you quit your job and hire a friend out of college that likes photography to handle the smaller events you don’t want to cover.

Boom. You’ve got a little photography business, and none of it was even remotely risky. You could sell it to a larger agency in town for around 1-year’s revenue, and save that cash for your next venture, or you could continue to grow it.

Example 2 - Sponsored Events

This is the story of one of the businesses I’m currently building. I’m not fully sustaining with it yet, but I’m on the way.

As it turns out, getting local corporate companies to sponsor certain events isn’t that hard. They do events regularly and pay a good amount from their marketing budgets to make them happen.

My business partner and I saw a lot of local startup entrepreneurs weren’t talking to each other, and they were too busy with their work. We created an event group called Moss Generation to host happy hours where we would invite ONLY startup entrepreneurs, and corporate groups loved it. They covered all the costs of drinks and food, just for the opportunity to attend and network with all the awesome business owners.

Eventually, we needed to be compensated for the work we were putting into growing this group, and so we started charging $2,000 per event. We take the money, and we cover the hosting costs with it, taking whatever was left for ourselves. We recently pulled that up to $3,000 as the events have gotten larger and more costly.

All I had to do was get in touch with awesome startup owners around town, that I already wanted to talk to, and invite them to the group. We figured out what they wanted in an event, and built our group around that. I started it with my business partner while I was in college, and it probably took 5 hours per week at the most.

The best part? We don’t even charge for ticket sales. There are probably 5 other groups in town that do similar things, and even though their attendees might not be as specific and valuable as ours, they’re even more successful than us and they make even more money off it because they charge for tickets.

You could start something very similar in your city. It doesn’t need to be a group of entrepreneurs. You could build a group of business students from local universities, and charge companies in town to hire from you. You could assemble nonprofit owners in town, and charge companies that might want to partner with them. You could just get cool people together in your spare time, and see where it goes like I did.


So, all you need to do is start. It’s not going to work the first time, but you’ll learn more than you did in any class. I tried to start at least 5 little businesses before I found something I was good at.

You’ve got a job. You don’t have a lot of time. But you do have an hour or two each weekend, or maybe half an hour during lunch each day. Use that time, send some emails, and try to get something started. Don’t jump in recklessly, and don’t expect to make a ton of cash off the bat.

As a final note, interview people. If you see someone running a business you think is super cool, ask to meet them over coffee. That’s how I got started when I couldn’t figure out how entrepreneurship functioned.

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