Chris Brogan, Small Biz Lady & More Give Advice For Coming Clean About Your Side Biz

It's the "Oh shit" feeling you get after being called into his office. It's your heart leaping into your throat when she mentions it after a meeting. It's the causal reference bomb he drops as he walks by your desk. It's finally happened: your boss has discovered your side business.

Chris Brogan, Chris Gullibeau on Side Businesses


For some, working a side hustle outside of office hours won't mean a thing, but for others with non-compete clauses and big responsibilities, things could start to get dicey from here on out. It's a new chapter in your corporate life. An era where you face suspicion of how you use your time on the clock — are you sneaking in your own work when you should be giving 100 percent to them?

Finding this competing passion project could be a cause of concern for your manager, and at the very least for you, sensations of nausea and panic. So what do you do when that moment arrives?

What do you do when your boss discovers your side gig?

I posed that exact question to a number of experts in the field on Twitter and via email. Experts who know a lot about starting their own wildly successful businesses and have risen to the top of their game by believing in themselves and their passion. Their answers give you a roadmap, a playbook, a step-by-step plan on how to handle the conversation and the aftermath. Check out what Chris Gullibeau, Ashley Ambirge, Gary Vaynerchuk, and others had to say about coming clean with your boss about your side business in this inaugural installment of a series I like to call 140 Character Interviews, below.


Chris Brogan — Human Business Works

"It's all in how you allow your outside work to conflict or not. If you're selling to the same customer as your day job, you're cooked."

Thinking strategically about your side-gig before you even start investing precious time, what's left of your energy, and buckets full of stress-related tears is step number one. If you want to keep your day job for as long as humanly possible (in order to eat and pay the bills while your startup takes off), make sure you're not stepping on anyone's toes. "If you're doing something very unrelated and you're doing the work I want you to do on my time, then it's not a big deal."


Gary Vaynerchuk — The Thank You Economy

"Panic. J/k. Don’t hide it."

Gary might be joking about panic, but that fight-or-flight feeling is real. Don't run. Instead, be honest. Being open about your side project is important to maintain a sense of trust between you and your boss.


Jenny Blake — Life After College

"Don't apologize but do be open (even proactive!) about talking w/your manager. Let them know you're still 100 percent focused and committed."

Once your side biz is out in the open, describe how you've partitioned your time to allow full focus on your day job and how you rock your side gig during the remaining 16 hours. You never know — your manager might even walk away impressed by your organizational prowess.

Get Chris Guillebeau, Melinda Emerson, and Ashley Ambirge's advice after the break.


Chris Guillebeau — The Art of Non-Conformity

"Tell your boss that your side project makes you a better employee because now you come to work because you want to, not because you have to."

This is your "drop the mic" moment right here. Chris goes on to say that according to research, employees — whether they have a side project or not — only spend a fraction of their day actually working. These stats could prove beneficial to you and the argument for your side gig. "Since you're devoting your spare time to the business, you're free to focus your 'employee time' on contributing in a substantial way to the company."


Melinda Emerson — The Small Biz Lady

"Be careful not to use company resources or your cellphone during business hours, as he or she is now watching you."

Now that things are out in the open, the air is clear, and you've laid out how you plan on keeping your corporate and solopreneurial life separate, it's time to stick to your word. Melinda advises, "what you do on your personal time is your business, but be careful not to be distracted at work." Using company resources — printers, phones, fax machines, time, and worst of all, computers — is off limits. Bring your laptop with you and take care of client emails, comments, and social media activities before you clock in or during your lunch break. Don't give your manager an excuse to doubt your commitment and you'll have a full-time, pay-the-bills job for as long as you need (or want) one.


Ashley Ambirge — The Middle Finger Project

"I'd ask him if he had any contacts who might need my help."

Ashley makes an interesting point here — why not ask your boss if there's any possibility of putting your skills to good use while on the job? Let's say you're in PR but want to flex your social media muscles (which just so happens to be the focus of your side business). Asking to incorporate more of that into your job description could at the very least get you some extra (paid) experience that you wouldn't have had before, while proving that you're still committed to the company. And hey, it'll look great on your resume, too.


What would you do if your boss discovered your side business? Share your thoughts, ideas, and comments below!


Source: Flickr user somedesignerguy (M11 Studios)