Get the FREE Freelancer’s ToolkitGet the free toolkit!

How To Not Let Money Hold You Back From Making The Leap


Tough subject.

We love it and we hate it.

It can buy us nice things, allow us to travel and see new things, keep the heat (or A/C) and lights on, and in many cases, help us find our freedom.

But right now, I hate it.

Why? Because I’ve been talking to a lot of people who are miserable in their day jobs and have bigger self-employed dreams for their life.

And for the vast majority of the time, the reason they don’t make the leap and make it happen is money.

I want you to think differently about money and your leap.

Here are 5 reasons why money shouldn’t be holding you back (in the way you think it does):

1.  You probably need less to live on than you realize.

Have you looked at your finances lately? Do you know how much goes out every month and on what?

I know, I know, looking at the nitty gritty details of how much you spend is the least exciting way to spend an afternoon. And it tends to make us feel bad.

But once you do, you might see a few things that can be removed from your expenses. Things you won’t miss for a short period.

Not only will removing those things mean you can save more to feel more confident in making your leap, but it will make it more clear to you how much you actually need to live comfortably in the worst case-scenario that you aren’t bringing in $$ from your business right away.

2. You have a lot more potential to make money on your own than you do in your current job.

Your current salary is probably stuck where it is. Sure, you might get a yearly raise, but let’s be honest, it’s never as much as you think it should be considering what you’re bringing to the table.

When you work for yourself, the sky’s the limit. You decide your prices, you decide how many clients you want to take on at a time, you decide how much you want to hustle to bring in new clients.

So get rid of that fear that you’ll never surpass your current salary. You can.

3. You won’t need big investments to make enough money in the beginning.

You don’t need a fancy website, fancy photos, ALL THE TOOLS to start. There are a million ways to bootstrap your business while still being professional and effective at what you do. I already talked about not needing it all to have it all here. And the freedom business you want to create (since you’re hangin’ out here) doesn’t require a lot of capital.

4. Your steady paycheck isn’t as secure as you realize.

People get laid off all the time. Companies down-size left and right. I have some stories about that here. We’ve even had a few FTF members who got laid off in the middle of preparing their leap. You bet they were glad they already started preparing for self-employment.

So why not start making your dreams a reality rather than wasting more time gripping that steady paycheck when it could disappear tomorrow.

5. Your current job doesn’t have to be your only money source until you make the leap.

You don’t have to go all-in. This is a big one.

  • If you find your job too stressful and at the end of the day have no energy to work on your side hustle, why not find a different job that is less demanding until you make the leap?
  • If you’re using all of your time off working on your side-hustle, and still aren’t building up enough income to make the leap, why not ask your boss to take it part-time or find another part-time job during the transition? (There are even some FTFers that took part-time jobs AFTER making the leap, both to take off a little of the financial pressure, and to be in a more social environment.)
  • If you have skills in a certain area, that are different from what your business will be, why not try to get some remote work in that area while building your primary business? (I know a lot of people that start out as Virtual Assistants as they make the transition into doing something else)

It doesn’t have to be all or nothing. You can ease into your leap as slowly as you feel comfortable, as long as you are taking action that gets you closer.

Now, I’m not advocating for ignoring your money, making un-wise financial decisions, and just quitting your job (although I’ve seen plenty of success-stories from people that do), but I want you to maybe take a look at your situation in a different way. There are options to re-arrange your current life and mindset to prepare for a better future.

Is money holding you back?

How can you change those money stories you have and start taking action towards your dreams?



Leah Kalamakis Leah Kalamakis is the founder of The Freelance To Freedom Project and a web designer/developer for brilliant entrepreneurs. When she’s not hanging out in the FTF Community, you can find her people watching on the streets of NYC. Come say hi on Twitter, Instagram, or Facebook.

+ get the FREE Freelancer’s Toolkit including:
✓ From Last Corporate Day to a Month of 5k
✓ How to Get to Steady
✓ 4 Steps to your First (or next!) Passive Income Stream Workbook
✓ Daily advice, tips & inspiration

Yes, please!

{ 7 comments… add one }
  • Love this Leah! I made the leap just a few months ago, but I’ll probably look for a part time job in a couple of months. Not only will it relieve some financial pressure, but I just moved cities so I’m definitely craving the social aspect and the opportunity to meet new people.

  • Knowing that bottom line number was a huge help in making the decision that I’m willing to take that risk.

    I realized that just one design projects per month is enough to get all my expenses covered.
    Knowing how many projects or clients you need takes a lot of the pressure off. You probably need less than you think!

  • Great post, Leah! So true, Nela. I’m in the process of transitioning to working for myself, and knowing my expenses and the number of articles/book sales I needed definitely took the pressure off, and made me realize it was possible.

  • The first part of this post completely describes me & I haven’t even been one of the people you’ve been talking to!
    I’ve kept a bank book since the age of 16 when I opened my first bank account. I detail every single thing in there and I plan what goes out every month so I know what I’ve got to work with. I couldn’t not keep an eye on my finances! As for salaries, don’t even get me started. I know I’m probably not the only one who says this when I deserve so much more for what I actually do. I’ve also been advised by everyone to not quit my job – so my freedom journey is going to be one of pure hustle! But one that I really want to do.

  • Money was the ONLY thing holding me back from quitting my job, so I definitely relate to this one. Prior to quitting, my husband and I paid off all our debt (except our mortgage), making it possible for us to survive on much less each month. That is what ultimately made it possible for us to live on just his income, so that I could stay home with our sons and build my business on the side.

  • As a single parent money is the ONLY reason I am not working on my business full-time. I currently have a well paid part-time job and without anyone else’s income to fall back on I’m not sure how to make the leap. I’ve pared back my spending but I simply don’t earn enough to save a buffer, so my only options are to just jump or take a more local, less well-paid part-time job that doesn’t use so much of my energy and forces me to up my game with my business. Meanwhile I’m investing in courses and looking for a business mentor…

Leave a Comment