We all love a good side hustle, right?

Who doesn’t love to do something on the side to make some extra cash AND feed our passions.  But, when does your side hustle turn into something a little bigger and have the potential to be your full-time job? 

This month, I left a position at the Wharton School at the University of Pennsylvania.  I know what you’re thinking… “what are you doing leaving a position at the number one business school in the country?”  Let me explain, I LOVED my job! I love the students, coworkers, and the institution BUT I was starting to love my side hustle more. My coaching business, equipping twenty somethings with the tools to thrive in both their personal and professional life, was taking off and the results I was getting from my own clients was incredible. Not to mention the flexibility to spend more time with the people I love and on self- care was unmatchable. I will say, I didn’t wake up one morning and decide my business was going to my full time gig.  I spent a lot of time deciding if this was what I wanted to do.  Was it silly to leave a job I loved to do something I loved more? If you’re thinking about taking the plunge to go out on your own whether full time or part-time, I challenge you to ask yourself the questions below.   These are the exact questions I asked myself before taking the leap.

What local or online resources do you plan to use?

Although I have worked with business students for many years, my education and training is in higher education and counseling.   I knew I needed something more and am currently taking a few courses and using local resources.  Small Business Development Centers offer some pretty incredible free or affordable services for new business owners.

How do you deal with uncertainty? 

I like to consider myself an unplanned, planner but in the world of business things go up and down pretty quickly.  One day things go as planned and the next a little crazy.  You have to be comfortable either going with the flow, using your back up plan, reaching out for support, or going on a little emotional rollercoaster.

Are your finances in order? 

This is really a personal decision on the finances front, but really take the step back and evaluate where you are.  Do you have clients or services lined up? If not, do you have another source of income for a few months? You need to have a game plan for where the money is coming in and at the very least how you are going to pay your bills until it starts flowing.  

How will you hold yourself accountable?

In many cases, you are your own boss.  What is your game plan for holding yourself accountable for tasks and determining what needs to be done and when?  It’s the worst just staring at your to-do list and being overwhelmed and feeling a little paralyzed.

How will you use and reach out to your support system?

We can’t do everything alone-it’s just a fact.  Finding people, you can trust and rely on is really important.  They can help you set priorities, listen to you go on your emotional roller coaster and provide some insight you may not have thought about.

What is your plan for self-care?

There is a lot of pressure either self-imposed or not to make your side hustle work but you can’t forget about self-care.  Make a plan for breaks, healthy meals, gym time, coffee dates with friends and whatever else you need to motivate you.  If you’re working in a solo business it can be a little lonely so make sure you’re getting out there.

When will you re-evaluate your plan?

Whether your business is thriving or not, set a date to check in with yourself and evaluate.  Is the business where you want it to be?  Are you still doing what you love?  Does something need to change? Do you need to hire some help? Taking the leap from side hustle to full time gig is not easy and it’s important to take the step back and ask yourself these questions.  If you decide now is not the right time, that is OK. It doesn’t mean in won’t be in a few months or year.  Just continue to ask yourself and check in to see where you are in the process. Are you starting to think about pursuing your side hustle full time?


Alissa Carpenter

Alissa Carpenter

Professional Trainer, Speaker and Career Coach at Everything's Not OK and That's OK
Alissa Carpenter offers professional development and career exploration to companies, alumni groups, student advising units, and individuals across the country. She works to enhance team communication, teamwork and interpersonal skills with an upbeat personality and true passion for working with others to set and achieve goals.Alissa has an MEd in Social and Comparative Analysis in Education, is a Gallup-Certified Clifton Strengths Coach and is certified in the Strong Interest inventory.
Alissa Carpenter

Latest posts by Alissa Carpenter (see all)