How I Gave Myself Permission To Try

It’s been over two years since I quit my job and started following a different path, making a living using my own wits, rather than relying on an employer for my livelihood. These days, I earn my living by writing and doing gig economy work. It’s not a glamourous life, but it’s an enjoyable one for me.

My life looks very different from what it used to look like. Two years ago, I could have counted on one hand the number of nice days I was able to enjoy during the workweek. These days, I spend almost all of my time outside, exploring the world and doing things that I find engaging and interesting. I like to think that I’m in the world now, rather than letting the world pass me by through an office window. 

Making this big leap wasn’t something I did overnight. It took years of work – work that came with no guarantees. In 2016, I launched this blog, and through the highs and the lows, I kept writing, trying my best to produce engaging content that could help and entertain people. By 2019, my writing was bringing in some decent income – not huge amounts of income, but enough that with my blog and side hustles, I’d probably be fine. 

Even when I got to that point though, I still had to push myself to make that last leap. There are countless people out there that have probably reached this same point. But maybe they haven’t made that last leap. They tell themselves they can’t make that final jump. Or at least they don’t give themselves permission to do so. 

That’s what it takes. You have to give yourself permission to try, even when you’re trying something with an uncertain outcome. Here’s how I gave myself that permission.

I Gave Myself A Cash Buffer 

When I wanted to make the leap to self-employment, I knew that I’d only have the guts to do it if I had a cash buffer in place. I come from the mindest of a risk-averse lawyer, so for me, I needed to have one year of expenses set aside to feel safe. If I didn’t earn a single dollar, I’d still be fine for a year. And if I could supplement my cash buffer with gig economy work, I could probably make it last another year or even longer depending on what I could make. 

It ended up working out well for me. In that first year, I rarely had to touch my cash buffer – I earned enough from the gig economy and this blog to keep that cash buffer intact. And while I had a feeling that would be the case – that I wouldn’t need to touch that cash buffer- having it there is what I needed to make the leap. Without it, I wouldn’t have had the guts to try to make it on my own.

A lot of people will tell you that keeping cash on hand isn’t smart. Mathematically, I get that – you can earn more on it by putting it somewhere else. There are ways to deal with this (using my 5% interest accounts system). But even without any money hacks, cash is still probably the most important thing you need if you want to do something outside your comfort zone. If you have cash, you can do a lot of things you might have told yourself you can’t do. 

I Reached Coast FIRE

Coast FIRE is the point in your financial independence journey when you’ve saved enough that, given enough time, you likely won’t have to save another dollar and will still have enough to support yourself at traditional retirement age. You can think of it as the tipping point in financial independence. Get to Coast FIRE, and things become much easier.

For example, imagine you’ve managed to save $200,000 by the time you’re 30 years old. Assuming you retire at 65 years old, that leaves you with 35 years for the money you’ve already invested to grow and compound. If you did nothing with that money and averaged a 7% rate of return per year, you’d end up with $2.1 million. It’s all thanks to the power of compound growth. Get enough money to start with, give yourself enough time, and your money can grow to unbelievable amounts. (I wrote a more detailed post about what Coast FIRE is here).

Coast FIRE is a powerful position to be in, which is why I tell people to live like a student early on and put their money away. When saving money becomes optional, you’re left with a lot more options. You don’t technically need to save for the future anymore. And if all you need to do is support yourself, there are almost no limits to what you can do. 

I put myself in a Coast FIRE position by accident a few years ago. I was so focused on reaching financial independence that it never occurred to me that maybe I didn’t have to get to my full financial independence number to go and do what I really wanted. When I realized I was at Coast FIRE, suddenly, I felt like I could give myself permission to try new things.  

I Created Backup Plans 

Life is far too fluid for any single plan to work. We all have ideas about how we want our lives to look, but it never happens exactly how we think. I started my legal career thinking I’d have a good career as an attorney for 30 or 40 years. But that didn’t work out. 

When I made the leap to self-employment, I wrote down several backup plans I had in case my self-employment journey didn’t work out. Most of my backup plans involved getting more schooling so I could get a different job. I told myself I could go to coding boot camp and get a job coding. Or I could get a library science degree and become a law librarian. Or worst-case scenario, I could probably go and get another job as a lawyer.

You can believe in yourself but also have backup plans. Backup plans aren’t a sign that you don’t believe in yourself. It’s just a sign that you’re giving yourself permission to try something and that if it doesn’t work, that’s okay too.

I Had A Spouse With A Good Career 

One thing that many business owners and self-employed people forget to mention is that they have supportive spouses that can earn income even if they fail. I’m no different. I’m married to a medical professional in a high-demand field. No matter what I earn, her income will likely always be enough to support our entire family (and it makes sense that it would be – she spent over half a million dollars to get this career).

Some naysayers will point out that this fact is why my story can’t apply to others. And perhaps there’s some truth to that. Not everyone can afford to take the chance to try something different. For many, their jobs might be the only way they can support their life. They’re paid just enough to be comfortable. 

But this can also be used as an excuse too. Some people will tell themselves they can’t try anything because they don’t have that perfect situation. The fact is, there’s never a perfect time to do anything. All you can do is be flexible, give yourself room to work with, and have the guts to try.

I Gave Myself Permission To Fail

Perhaps the most important thing I did was to tell myself that it was alright to fail. I think this is something that holds many of us back more than anything. Putting yourself out there is scary. It’s a very visible thing when you bet on yourself. There’s no shortage of people who will tell you what a mistake you’re making. And if you fail, plenty of people will laugh and tell you that they told you so. 

You have to give yourself the permission to fail if you want to give yourself permission to try anything. You’re always going to suck at anything when you start. And everything you start won’t work out either. 

That’s okay though. Roll with the punches. When I went all-in on myself, I knew I might not make it. I might have to go back and get a job. I still might have to do that. If it happens, I know I’ll get ridiculed for trying. 

You have to accept that some people will cheer if you fail. And you very well might fail too. If you can’t accept that, you’ll never try.