Moonlighting: 13 Steps to Get Started

Why it Matters: Missing key steps in the set up of your moonlighting venture could land you in hot water — or create such a miserable experience that you give up on your dream before you’re even out of the starting gate.?

Here are 13 steps to set you up for success with your moonlighting hustle...

#1. Read Your Company's HR Policies.

Most companies today have policies addressing their employees doing side hustles, working secondary jobs, and having their own businesses. Failure to follow these policies could cost you your job.

#2. Learn the Ins and Outs of "Work For Hire."

Work for hire rules can be complicated. This article gives a helpful explanation. The key is to ensure that anything you create remains your intellectual property versus the IP of your employer. Discuss with your attorney.

#3. Set Up Your Business LLC or Other Legal Entity.

Don't overthink your business name. You can always operate as a DBA (doing business as) later. In addition to the financial and legal benefits of establishing a legal business entity, treating your business like a business — and not just a hobby — goes a long way to building your CEO mindset.

#4. Meet With Your Tax Accountant.

Tell them what you're planning so they can advise you on how to keep your moonlighting income and expenses accurately tracked and separated. They can also help you plan for your quarterly tax payments that will be due (or whatever cadence required in your home country).

#5. Set Up a Business Checking Account.

You'll need your business entity paperwork (i.e. LLC filing) completed to do this step. If you don't want your clients to treat you as an independent contractor (IC), but rather as a "real" business, you need a business bank account.

Think about it this way: from your corporate client's end of the table, it matters whether they are paying a company or paying an individual. In fact, many U.S. companies have rules stipulating they will not pay an independent contractor more than say 500 hours in a year because otherwise it opens them up to accusations the IC was actually an employee and thus entitled to benefits.

There are also legal, financial, and CEO mindset benefits to keeping your business money separated from your personal money.

#6. Get a Credit Card Just for Your Business.

Keeping your business expenses separated makes it easier to keep track for tax purposes. More importantly, it will help you establish a CEO mindset. For example, if you are ever tempted to discount your services, you'll easily be able to see the operating and overhead expenses of your company and can remind yourself you're not running a charity.

#7. Buy a Separate Laptop. Set up a Dedicated Email.

Don't conduct any of your business' work on your employer's computer or through their email account. You can use a gmail-based account. But spring for a BRANDED email address, not an @gmail.com one.

#8. Hire a Business Attorney in Your State, Province, etc.

Yes, you'll need a trusted, go-to attorney. Be sure to find one who is familiar with the type of moonlighting you'll be doing (i.e. consulting, communications, coaching, training, etc.). The first thing you need from them is a business contract for your work with clients. Do not work with a client without a contract in place.

#9. Fish in a Different Pond.

We recommend keeping your moonlighting on the "down low" in terms of your employer. While you may have to disclose it to HR, waving your side hustle in their face is not good for your career track.

With that in mind, when looking for clients, you'll want to fish in a different pond than folks who are connected in some way to your 9 to 5.

Pick up the phone and call old co-workers and bosses, friends and family, and other personal connections. Let them know what you're available to help with. Keep calling people until you have your first client project.

#10. Give Yourself Extra, Extra Long Deadlines.

The only thing predictable about work emergencies and personal emergencies is that they are bound to happen at the worst possible times.

When you already have a demanding full-time position, you need to give yourself extra, extra, extra (did we say extra?) time on your client-facing deliverables. And then proceed to getting everything done long before those actual deadlines.

#11. Track Your Success Metrics at Work.

Don't rely on your memory. Start tracking your metrics now. If there are metrics you didn't track related to important accomplishments under your watch, use the time while you're still employed to go back and get those numbers.

When you are just getting started in your business, this professional track record will serve as your "proof" of credibility.

• How much budget are you managing in terms of dollars?
• How many people are you managing?
• What has been the bottom-line impact of projects you're leading? Revenue wise? Cost savings wise? Industry reputation wise? Etc.
• How many people (employees, customers, etc.) are impacted by the various key initiatives that you're spearheading?
• What solutions have you innovated and implemented?
• What is your on-time completion rate of projects?
• What is your success rate of projects?
• How many people have you presented to?
• How many hours of experience do you have doing X?
• What awards have you won? (Hint: Now is the time to start applying if you aren't already!)
• What else does your department or company track? What else can you possibly measure to capture the scale of your expertise? Capture it all!

#12. Proactively Build Your Professional Network.

While still employed, you are operating from the "inside." That gives you a leg-up in building an expanded professional network, which will turn into your million-dollar Rolodex when you strike it out on your own full time.

Build your network:

• With both mid-level and top leaders all across your existing organization.
• With your peers at all of your strategic alliance partners, subsidiaries, vendors, suppliers, service providers, and all other companies that are in your current employer's ecosystem.
• With your peers at your competitors.
• By attending industry conferences and professional conferences.

Now is also a GREAT time to speak at industry and professional conferences. Because you are not yet a consultant or a service provider, but rather speaking on behalf of an organization, your chances of getting booked are sky high.

This will not only expand your visibility, it will also build your thought leadership platform for when you fully launch your business.

#13. Join a Mastermind & Find Your Community.

You are your business's most valuable asset. Don't go cheap with free business coaching or a one-hour-per-month type of a coach. When you are striking out on your own, it's essential to fully immerse yourself into the world of entrepreneurship. Making this investment while you're still employed and not stressed out about revenue coming in the door is a smart idea.

The key is to find a community that is 100% aligned with the type of business you are starting.

For example, the BoldHaus Collective is 100% dedicated to experts who provide services to corporate clients as well as other organizations, such as nonprofits, universities, mid-markets and other B2B type clients. Being with others who "get" your type of work is absolutely critical.

Final Take-Away: Making the leap to full-time entrepreneurship will always feel a little scary. So get crystal clear going into your moonlighting venture about what "proof" or confirmation you're looking for, exactly, in order to make that final go/no-go decision.

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