Should You Quit Your Job To Become An IT Entrepreneur?

By Carrie Dagenhard (Tech Writer)

Should you leave your nine-to-five job to become an IT entrepreneur? Here are some very important questions to ask yourself before you make the leap.

We all have bad days — days when you’re overwhelmed by your workload, frustrated by poor leadership support, and irritated by a lack of appreciation or recognition. In those moments, you might imagine submitting your two-week notice and walking triumphantly into a life of self-employment. Body 1

After all, as an IT pro, you have a laundry list of highly marketable, in-demand skills. Not to mention, the idea of entrepreneurship can be highly enticing. (Especially if you go by the social media highlight reel of six-car garages and perpetual vacations.)

But, should you really jump ship and join the millions of self-employed professionals?

Before you make the leap, here are five things you need to consider.

Do You Have A Financial Safety Net?

Sure, many IT entrepreneurs are raking in a cushy seven figures (or more), but there are also plenty living in their parents’ basement. Before you dive into self-employment, it’s critical you evaluate your finances. A good rule-of-thumb is to save at least six months’ worth of living expenses, should you need to draw on savings to cover living expenses and health insurance while you spin up your business. And, even after you’ve amassed a healthy client-base, it’s crucial you have a safety net (just in case you suddenly lose a chunk of work).

If you don’t already have a safety net, consider picking up a side gig to bring in extra cash and build up your savings while you test out the self-employment waters.

Have You Identified Your Niche? 

What sort of work will you do? What will your clients look like? Before you cut ties with your employer, take time to determine what types of companies you want to work with or where you have the most experience. For example, you might specialize in IT for healthcare, IT for small businesses, IT for the energy sector, etc.
body 2
Narrowing down your niche allows you to hone your expertise further and illustrates to potential clients that you understand the challenges specific to their industry. While you may think being a “jack of all trades” will bring in the most work, it’s better to focus on one or two verticals. Clients want IT experts with a firm grasp of their unique pain points and a history of overcoming them.

Do You Know How You’ll Find Clients?


Tapping Your Network

Reach out to former colleagues and contacts in your industry and let them know you’re spinning up your own business. If they don’t have work for you, they may be able to direct you to people within their network who have a need you can fulfill.


From email campaigns to advertising across social media and professional networking sites, participating in educational webinars, to blogging, there are many ways to market your business as an IT entrepreneur. If you’ve never worked in marketing, it’s a good idea to partner with a consultant or agency who can help, lest you waste lots of money spinning your wheels.


Have you impressed a client? Ask them for a recommendation, and let them know you’re grateful for referrals to other potential clients. Depending on your financial circumstances, you may even incentivize referrals with a reward — like a gift card or percentage off your services.

Have You Talked To Other IT Entrepreneurs?

Entrepreneurship isn’t for everyone. Some people thrive while working for themselves, and some people quickly discover they loathe it. Before you leave the safety of your nine-to-five, chat with a few other IT entrepreneurs to learn about the positives and negatives of owning your own business. Ask them what they love, what they hate, and what advice they have for you as you decide the future of your career path.

It’s also a good idea to talk to a CPA and a small business attorney about the financial and legal aspects of business ownership to make sure it’s something you’re ready to take on.

Will You Need To Hire Employees?

As you create your business plan, you’ll need to decide whether the workload is something you can manage alone, or if you’ll need to bring in a partner or hire additional IT pros. One of the worst mistakes you can make as a new entrepreneur is to bite off more than you can chew and end up delivering subpar service. If you’re not ready to bring anyone else in, make sure you’re not taking on too much.

Leaving the safety and security of a full-time job to launch your own business is exhilarating — and while there’s a tremendous opportunity for success, there are plenty of challenges, too. (Check out this article by SherpaDesk CEO Patrick Clements about his experience building his business and the challenges he encountered along the way.) By taking the time to consider these questions, you’ll be better prepared no matter what you decide.

SherpaDesk is the definitive helpdesk solution for all your support, project management, and billing issues. 

Ready to get a handle on your small business? 

Power your helpdesk with your Free Online SherpaDesk Support Desk Software.


Sign Up for Our Blog Updates and Stay
on Top of the Latest News and Tips


Carrie Dagenhard
By Carrie Dagenhard

Carrie specializes in technology storytelling while residing in the "Silicon Hills" of Austin, TX.