Guest post by Kamara Toffolo, Career and Leadership Coach


So you’ve decided to build a business!  Congrats!  And you want to keep your day job while you’re growing?  *fist bump* That’s one of the best decisions you could have made in your entrepreneurial journey.  Though you’ll be strapped for time, you won’t be as strapped for cash like your quit-today-fly-by-the-seat-of-their-pants counterparts.

You’re not going to be one of those entrepreneurs in a do or die situation.  No, not you.  If entrepreneurship were a race, you’re the tortoise and the other guys, they’re the hares.  You’re slow and steady and you will win the race.  You’re allowing yourself the opportunity to really plan things and really scope out your biz while the other guys are throwing spaghetti at the wall and seeing what sticks. And you have the ability to create yourself a financial cushion so when you do take the leap, you’ll be able to support yourself should you encounter your worst case scenario.  You, my friend, are the epitome of pragmatic.

Though your approach to work-freedom is sensible and calculated, it isn’t without stress.  The road of entrepreneurship is a lonely one.  Sometimes you’re seriously going to want to drop your aspirations because it is hard.  It is so, so hard.  It will always be hard.  This isn’t work for the faint of heart.  This is work for the bravest among us.  You’ll notice that as an entrepreneur who is also working a day job, you’ll have your own unique stress. Here are the four unique side-hustle stressors to be on the lookout for.




You’ll feel like you have multiple personalities

Sometimes you won’t know if you’re coming or going.  Am I in day job mode or am I in entrepreneur mode?  You’ll wonder who you show up as in all aspects of life.  You’ll sometimes feel like you have multiple personalities.  Well, you do.  You can’t possibly be the same person at the day job as you are in your business.  In the day job your role fits a certain box.  Sure you might take initiative and stretch outside it, but not the in the same way that you’ll stretch yourself in your business where you are responsible for EVERYTHING.  The day job has limitations.  The business is only limited to the extent that you limit yourself.  Embrace your multitude of personalities.  They are the keys to your success.

You’ll be paranoid of being found out

When I first started building my coaching practice, I was beyond nervous about being found out by my employer. The worst case scenario always played in my head – my boss calling me into her office with my website up on her computer and immediately being handed my walking papers.  Of course, when thinking rationally I realize that they would have been hard-pressed to fire me for having a side gig that had absolutely nothing to do with the industry I was in.  Job security aside, I also knew once I was found out, I would get my fair share of unsolicited advice from people who had no idea what it was like to be an entrepreneur.  I simply didn’t want that energy suck.  So I protected my coaching practice and its identity.  I never spoke of it in the office.  For the three people that did know about it, I’d only discuss it in general terms.  No one had any idea how my business was doing, and it needed to be that way for survival.

You’ll feel misunderstood

Entrepreneurship changes you in a big way.  It’s a journey that allows you to really get to know yourself at a deep level.  It teaches you about your purpose and passion and how freakin’ badly you really want to do what you’re doing.  You will harness strength and tenacity you didn’t know you had in you, and that will change your outlook on many things.  Most of your family and friends won’t get this.  They’re too used to knowing you as corporate employee.  When you try to explain the really great and amazing things that you are doing as an entrepreneur, you’ll get a lot of blank stares.  From the boldest of the bunch they might even try to talk you out of your dreams.  You also may have loved ones distance themselves because they are just so confused they don’t know what to ask.  This might hurt you.  This might make you feel misunderstood and unsupported.  But you’re an entrepreneur.  You are courageous.  Even when no one seems like they’re on your side, don’t stop.  Don’t you ever stop.

You’ll be really, REALLY, tired

Hello bags under the eyes!  Nice to meet you new friends!  While you’re working during the day, and moonlighting as an entrepreneur, you are going to be working harder than you ever have before.  You will be putting in countless hours.  Days will start to blur together.  You might forget to eat, you might not get much sleep, you might look like a pile of shit.  This, my friend, is temporary pain.  You are setting the stage for when you can confidently step into your business full time, and step out and away from your day job.  The sacrifices are necessary.  The pay-off is infinite.

Nothing about this journey is easy.  You’re going to fail.  You’re going to suffer.  You’re going to hurt.  Your friends and family won’t understand what you’re doing, and they might not even support you.  But keep your eyes on the prize.  Stay focused.  Keep moving.  Then when you finally get to work solely on your dream, look back to see how far you’ve come and revel in your accomplishments.  You’ve earned them.



Kamara Toffolo is a Career and Leadership Coach for Corporate Misfits!  She helps working professionals either commit to or quit corporate by figuring out what work WORKS for them.  Whether they want to excel in the corporate world or follow their hearts and break-free from the rise and grind, Kamara helps her clients get clear on what they want so they can go out and get it!  You can find Kamara at https://kamaratoffolo.com and also on Twitter, Facebook and Instagram​.