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This is what it takes to work a 9 to 5 & build a side hustle.

For the past year I have been building several side businesses while working a 9 to 5 that requires considerable travel, hustle and commitment and ya know what?

It sucks!

Big time.

I have been reading a lot of articles lately that glamorize the hustle and the grind of entrepreneurship but when it comes down to it, it is anything but glamorous. It’s even less glamorous when you are weighing its demands with those of a full time 9 to 5.

It is coming home from a 16 hour day exhausted but knowing that you have another 6 hours of work ahead of you.

It’s balancing the to-do lists of two commitments in your head.

It’s scrambling to do business calls during your lunch break.

It’s taking advantage of every single waking moment of your day.

But ya know what? Working a 9 to 5 and building a side hustle is totally worth it.

I call it “entrepreneurship training wheels” and it is the ideal environment for learning whether you have what it takes to jump headfirst into entrepreneurship OR to stay within the confines of your corporate pursuits. Either way, it’s up to you and your aspirations, but having a 9 to 5 to support yourself while you figure this out creates an environment to learn, pivot and move forward.

During the day, I work in Chicago for a technology company that I love. I am passionate about what I do and the people I work with. But, I have always wanted more.

During the night, I run my side hustles which include a podcast, an e-commerce line, a daily online publication, a series of webinars and video courses, and more.

This is what I have learned it takes to build a side hustle while working full time.


Above: me in Chicago pondering if it’s all worth it. (Answer: YES)

You have to commit.

Think I’m about to say that you need to commit to your side hustle? Kinda.

It’s really exciting to start your side hustle. You have the whole world ahead of you, you are confident you’ll be able to make 6 figures in your first 3 months, quit your corporate job and you’ll be on the cover of Forbes Magazine in no time.

Time to wake up.

I hate to break it to you, but that is simply not going to happen. I am all for dreaming big and creating a vision for your hustle, but in 99% of cases, your side hustle is going to be a grind that is going to take time to develop and scale.

Dream big but be realistic about what it is going to take.

I fell into the latter way of thinking early on and it started to affect my performance at my day job. I was so confident that I would be able to scale my side gig that I felt that I was biding my time at my 9 to 5 until I quit.

So, when I say commit, I actually mean  – commit to your day job. Commit to that which is paying the bills and allowing you to work on your side hustle. You never know what might happen, so don’t jeopardize your means to live and financially support yourself by being overconfident.

Know the vision for your hustle and work towards it but make sure you are still committed to your day job.

Work that 9 to 5, commit to it and then hustle your face off from 7 pm to 2 am.

No more Netflix.

Think about what you normally do when you got home from your 9 to 5.

Netflix? Relax and read? Workout and shopping? Nothing at all?

Not happening anymore. You’re going to have to get creative with your schedule and you’re going to have to make a lot of sacrifices.

I don’t watch TV, I don’t go out on weeknights, I don’t go to the movies. I get home and I switch gears from corporate mode to entrepreneur mode. No excuses and no exceptions.

I am a single guy living in Chicago so I can only imagine what this sacrifice looks like for a married man or woman with children but I will tell you this. It is a sacrifice when you compare it to what you would normally be doing after work, but it is not a sacrifice if you’re passionate about what you are building.

I don’t want to get into chasing your passion and doing what you love, but I will tell you that you won’t even think twice about making these sacrifices if your side hustle is something that lights a fire inside of you. I don’t think twice about not watching TV or hanging out on a weeknight. It is a no-brainer for me that I will be working on my side hustle because I believe in it that strongly.

Think happy thoughts.

Everyone starts their side hustle with unhindered optimism and positivity that their efforts are going to create life changing ROI. While that might be true in the long run, it is not going to happen immediately.

You will undoubtedly run into countless roadblocks, mess ups, tweaks, pivots and rebrands and it will start to weigh on you.

You will go into the red, lose confidence in what you are doing and think about abandoning it all.

That is why it is always important to maintain a positive attitude.

I am positive to the point of comedy.

Lost money last week? I am positive that my next optimization and tweak will get us back on track.

Not receiving positive feedback on a new release? I am confident that the next version I release will be the best yet.

This is the kind of positivity you need to have at every step. It fuels my ability to get punched in the face, knocked down and get up for another round. Take it step by step and have confidence that the small moves you are making will take you to where you want to be.

Don’t bring it home with you.

Working a 9 to 5 alone can lead to a lot of stress in life. You hear it all the time: leave work at work.

When it comes to your side hustle, you need to commit to doing just that – leave your day job at the office. If you bring the stress of your 9 to 5 home with you, it will have a ripple effect on your side hustle.

Don’t let that happen. Leave that sh*t at the office. And visa versa. Don’t bring the stress of your side hustle to the office.

This is easier said than done but I have found it very beneficial to your mental health to learn to compartmentalize these endeavors and the feelings they create.

Don’t do it yourself.

You don’t have 12 hours a day to dedicate to your side hustle. I wish I did but that will not happen until you decide to commit 100% to it. You will need to find a way to focus your efforts where you are most capable and effective and let someone take care of the rest.

Time is currency.

I am a big advocate of outsourcing tasks and skills to make you overall more efficient. I do this with various elements of my businesses from creative services to certain bookkeeping and financial matters.

Outsource certain elements of your side hustle (budgets allowing, of course) so that when you’re working your 9 to 5, your side hustle is still running. This doesn’t require vast budgets or a complex workflow/org chart. Hire a virtual assistant to help you process orders, a young and hungry college student to help run your social media, or a freelance marketer to assist with your media plan. Whatever it is, be smart with who you hire so that you can trust they are getting the job done while you work your 9 to 5.

Party on.

Take some time off.

Seriously. When you are grinding both a 9 to 5 and a side hustle, you will start to burn the candle at both ends.

Find times during the week or the weekend where you can decompress and unwind. I personally found this very difficult to do and as a result, I sometimes find myself consumed by the hustle and it can have negative mental effects on myself and my relationships.

Find time for yourself – whether its going to gym (leave your phone behind!), going out for a bit, or simple getting out of the office or your home creative space.

I’d love to hear your strategies for crushing your day job while creating your side hustle. Email me…

Image credit: pexels

Written by Case Kenny

Case is the Founder and Editor-in-Chief of and the host of the New Mindset, Who Dis podcast. Reach him at or @case.kenny on Instagram.

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