So You Want To Quit Your Job and Start Over? You can do it, I did.

by | Jun 6, 2019

There are plenty of barriers to becoming your own boss: student loans to pay off, bills to pay, family obligations and responsibilities and perhaps other people’s expectations to fulfill. For me, it was far too easy to come up with dozens of excuses as to why I couldn’t take a risk. For one, it’s risky. What if I can’t pay my bills? What will my friends think? What will my family think? What if I fail? BUT what are the potential rewards? What if I’m finally happy? What if I finally wake up to do what I love and it doesn’t feel like work at all? You have to overcome the FEAR.

Understand that getting what you want is going to take a lot of work. Nothing in this life comes easy – I’ve learned that. But your happiness is worth a lot. Think of how hard you work right now for someone else. Wouldn’t you be willing to work that hard for yourself, knowing that the benefits are so much more?! So, start planning your escape route – you can do it!

Save and plan.

Start to write up your plan for transitioning into your new life path. It can be gradual. Maybe you are lucky enough to have a lot saved and you can tell your boss that you quit tomorrow – but if you’re like most Americans, you don’t have much in the piggy bank, so it’s time to save and plan out a strategy for becoming self-employed.

Know your lifestyle.

Make a list of your monthly expenses. Yup, all those Starbucks trips and doggy daycare reservations count. Write down everything from groceries to hair appointments; from diapers to mani/pedis; gasoline to girl’s night out. You’ll probably be shocked to see where all your hard earned money is going! I know I was. I had no idea how much I was spending on eating meals out until I wrote it all down and signed up for’s free budgeting service. Know your monthly budget and learn how much money you need to earn to pay all of your basic expenses: rent/mortgage, food, phone, car etc. Anything else is a luxury right now.

Make a change.

Here’s the tough part – are you willing to make some sacrifices along the way for your ultimate dream goal of doing what you love? Depending on how healthy your savings account is at this stage in your life, or if you have a partner or family member that can help support you during this time, you may have to trim the fat from your daily spending. Bring your lunch to work – make your coffee or tea at home and take it on the road. Let your roots grow out for a couple of extra months! Some things you can’t afford to skimp on – feeding your family and taking care of emergencies are part of life, but we can always cut back on shopping, pampering and some of the unnecessary extras. Fret not – it’s only temporary and it’s going to be worth it.

Lay the foundation.

I started teaching fitness classes as a side job and I studied for my certifications on nights and weekends. Whatever it is that you want to do, do as much of it as you can in your free time and start building your skills and potential clients.

Get funded.

Some of you may need a lot of “start-up” money to make your dreams a reality. Not everyone can ask family members for money, so investigate all of your options. Look for grants and loans specifically for start-up businesses – there is money out there. Check out for information on funding your small business. Don’t be afraid to visit your local Chamber of Commerce or other small business organizations for tips on where to go for funding. There lots of cities and towns that have money available to artists, farmers, women and minorities (just to name a few).


This is really difficult for some people. You have to believe in yourself and believe that you are worthy of other people’s attention and money! Start a Facebook and Instagram page, start a blog or website, make business cards and get the word out about yourself. You are awesome and amazing – believe in yourself and you will go far. Half the battle is getting the word about what it is you do – then of course you have to be able to deliver the goods.

Finally: cut the cord.

Talk to your boss about your plans – write that resignation letter. It will be the greatest and scariest feeling of your life. Plan out those last few weeks or months and then devote your efforts full time to your dream.
Good luck, dream big and work hard.