90-Day Checklist: How to Finally Get Ahead and Be Your Own Boss

be the boss checklist

In January 2013 I made it my New Year’s resolution to quit my job and become my own boss. My life was changing in a lot of ways and I needed more financial freedom and flexibility.

I ended up quitting my accounting day job on May 1, 2013 and never looked back. Since then I’ve become the breadwinner for my husband and I, and we recently moved from Texas to Colorado.

If your New Year’s resolution is to finally get ahead, quit your job and be your own boss this year, here are six steps to take that will help you reach your goal.

Spend 90 days tracking your situation

The first step towards becoming your own boss is taking inventory of your financial situation. Yes, I know this isn’t a fun thing to do but there’s one way to make it less painful.

Instead of doing what experts say and starting with a budget and cutting out all your excessive spending, start tracking your income and spending for the next 90 days.

Don’t make any drastic cuts or changes to your finances, just track your buying habits and income, then take inventory of them in 3 months.

This will help you see what kind of spender or saver you are and reveal where your priorities are out of whack. Even if you’re sure of where everything stands it doesn’t hurt to re-evaluate what you value most.

I have personally done experiments and know that it takes a solid 90 days before changes to my work routine, budget or any other habit, actually produces results.

Prioritize your debts first

Once the 90 days are up, you can start putting together an accurate budget (I highly recommend trying out the Mindful Budgeting Planner), with the information you gathered during the past 3 months.

Put your debts at the top of the list, even before paying your other bills. Why? Well, I personally hate debt and think it’s the fastest way to derail your life and money goals.

But aside from that, it’s very costly because it sticks around for a long time (especially student loan debt) and you have to pay tons of interest and annual fees. It’s just not worth it!

When I was in the process of quitting my job, the first I did was add up all $14,000 of consumer debt, my take-home pay and monthly expenses. Being your own boss comes with a lot of ups-and-downs so paying off debt and getting control of your spending is key to reaching that goal.

Next, I created a debt payoff plan that allowed me to be debt free in just over a year. You can do this too by utilizing several resources:

  • Budget planner or expense tracker – There are several options available for tracking your expenses and compiling a budget. Some of them are digital, like Mint.com or You Need a Budget, or more old school like the Mindful Budgeting Planner or a simple spreadsheet. Choose one that best fits your needs and start writing down your expenses every week.
  • Debt calculator and payment plans – You don’t have to come up with a debt payment plan on your own, there are multiple resources and apps that will help you do this. Check out ReadyForZero or this debt calculator from CNN. Prioritize your debt payments first then other bills and savings next.
  • Refinancing options – You can save a good bit of money on interest payments and fees by searching for refinancing options to lower your debt payments. LendEDU is one startup looking to help student loan borrowers, specifically, by comparing many of the companies who offer student loan refinancing options. With LendEDU, you can sort through many different options all in one place.

Side hustle on your own time

During the 90 days when you’re simply writing down what you buy, use this time to increase your income as well. Start freelancing or working multiple jobs in the evenings and on weekends.

There’s only so many ways you can cut and trim your expenses until you have to start earning more money to make a bigger impact. What other skills do you possess that you can leverage into earning more money?

Use your freelance skills to bring additional money outside of your 9-5 job with TaskRabbit or Fiverr. Turn your hobby into a side hustle. Use sites like Etsy or eBay to sell goods, or become part of freelance communities like The Careful Cents Club or Freelancers Union.

For two years, during nights and on weekends, I worked at a local tax office in addition to my accounting day job. This allowed me to pay off the $14,000 of credit card debt in just over a year and start saving money towards my “quitting” fund.

quitting job quote

Create a (fun!) plan to quit

Wanting to quit your job is a scary (but admirable) thing. But don’t stop there! Spend this time creating a solid plan to quit your job.

Use this time to experiment and practice what it will be like living without your steady paycheck coming in. Devise several contingency plans and multiple avenues if you need a back up plan.

Make it a fun process! When I created my own plan to quit my job I sketched out some fun ideas and even put together a vision board to visually represent what I was aiming for.

Name your goal something catchy and find fun ways to motivate yourself during this time. Open up a separate bank account using your goal’s name. Sometimes finance or career plans can get boring so it’s important to keep your momentum moving forward.

Do a practice run

Can you pay all of your bills and fund your new business venture with the money you have saved and the income you’re earning from side hustles? There’s only one way to find out!

Do a practice run of paying your bills and funding your business using only the income you bring in outside of your day job. For the one full month test out whether or not you can survive and create a contingency plan if things don’t go just right.

Any paychecks you earn from your day job can be banked into your “Leap Fund” and you’ll get a better sense of whether or not quitting your job is actually doable. In addition, it makes taking the leap less scary now that you’ve done a practice run.

Limit the amount of bridges you burn

As you begin the process of quitting your job, the main objective to remember is to not burn those bridges. Maintain positive business relationships with your coworkers and boss, because they could potentially become your first clients.

At the very least they can help refer new clients and contacts your way, so you want to make sure to continue fostering those relationships. Finally, give your boss plenty of notice before you decide to quit — I gave my boss 4 full months’ notice.

Starting your own business is an exciting time, but don’t forget to make smart financial moves that will set you on the path towards success.

Here’s your 90-day checklist so you can jumpstart the new year and finally get ahead.

  1. Track your spending and income (no budgets allowed!)
  2. Prioritize debt payments first and find ways to save on fees
  3. Work multiple jobs in the evenings and on weekends
  4. Create a plan to quit your job and open a separate bank account
  5. Do a practice run and try to live on the money you’re earning outside of your job
  6. Put in your two week’s notice but don’t burn bridges when you leave

The next 3 months are going to go by anyway, so why not make them awesome?

What’s your plan for finally getting on top of your goals? How are you turning your resolutions into action?

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  1. Robert says:

    This is a comprehensive yet wonderful list, Carrie. It is always important to weigh the benefits and risks associated with quitting your “stable” job to follow a passion like freelancing. Being your own boss has its rewards but one does not want to get caught up in the excitement and forget about the important aspects both before quitting and after. Great post!

  2. Shirria says:

    I like that you provided real advice. I’ve come across some bloggers and social media personalitites that make it sound as if they quit their job and their was magically different the next day. I like that you are giving realistic advice with strategic steps to take to achieve work independence if desired.

  3. Rachel says:

    Thanks Carrie for this insight. I love the fact that you listed everything out and gave some examples of who to start with in your article. I am researching them as we speak! Can’t wait to start tracking! Even if I don’t quit my day job for a while, it is still a good idea to track your spending for 90 days in general to see where your spending habits are and plan for the future. Thanks so much.

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