It’s been two years since I left my full time job to work for myself full time, and there have been lots of up’s and lots of down’s.

Looking back and learning from the mistakes I’ve made have shifted my perspective to 1) enjoy + be grateful for the present, and 2) prepare for my future.

I wanted to share a few of the lessons I’ve learned in hopes to provide some insight and some inspiration for those of you who have hopes of doing the same.




1. It’s not always fun and games.

My first thought when I quit my job was, ‘YAY! Now I can go do whatever I want and finally make use of my days instead of spending every single hour of sunlight locked in a cubicle surrounded by people who made me miserable!’

Two weeks later, I’m trying to figure out how I’m going to pay my rent for the next three months. Welcome, anxiety.

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You see, it’s not always fun and games. There is no such thing as an absence of problems.

People have this idea that freelancing or entrepreneurship is the solution to all of their problems – but they forget to consider the sacrifices that are made in the pursuit of working for yourself full time.

You’re not getting away from all problems, you’re trading in your old ones for different ones.

Don’t be naive and think that you won’t run into stressful times just because you left behind a job that you hated in search of a dream – knowing this, and preparing for this, will ensure that you don’t give up when things get tough, or don’t necessarily go your way.


2. There are no off hours.

in the sky project inspo

That 9-5 work day is going to seem like a piece of cake when you’re sitting in front of your computer, still working at 4 o’clock in the morning. Think you had long nights before? Well, there will be longer nights.

There have been weeks where I’ve worked 15-hour days for five days straight. I work on weekends. I work at night, I work in the afternoon, and I work in the morning. I work whenever and wherever I can. Because if I don’t work, I don’t make money.

The great thing, though – is that I have the flexibility of working when I want, and where I want.

Staying productive and staying creative despite working long hours is a battle that you’ll always be fighting (READ: 5 Ways To Stay Productive + Get More Stuffy Done), but having the option to work at a coffee shop on a Tuesday, or in your pajamas in bed on a Friday, is an option I’m glad I get to have.


3. You better save that money, honey.

‘Cause tax season is coming for you. I used to look forward to tax season because I got a fat refund check come around like a piece of cake when I’m on my period.

But when you’re working for yourself?  You’re the one paying the government.

I’ve had to be smarter about my spending, and anticipate how much money I’d have to save to eventually pay up when tax time came.

But thank goodness for the internet, mentors and do-it-yourself tax software like TurboTax.

turbo tax | taxes

My father was an entrepreneur and ran several of his own businesses for over 30 years.  Every year, I’d see him going through expense receipts, calculator on his desk, and forms being filled out with TurboTax on his computer screen.  He did all of his taxes by himself, every single year, with TurboTax.


This year, I’m deciding to do my own taxes for the very first time, and I think my pops would be proud. He may also be a bit jealous with all of the new, seamless and time-saving ways to do them, thanks to technology.

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There’s a mobile app that lets you start your taxes, estimate your refunds and track donations all on your phone.

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Whether you’re working for yourself, or working for the big man – more people are doing their own taxes. Yep, 5 million Americans filed their federal and state taxes last year for free with TurboTax Absolute Zeroand I’ll be one of them this year. 


4. There is actually a reason why you did all that b-tch work.

Everything you thought you didn’t need to know at your past jobs, ends up helping you in your new career.

Cliche, isn’t it?

All of those horrible powerpoint presentations that never got used, all of those hours spent researching something I had no idea why – back then, I thought it was all a waste of time. It added to why I became so frustrated working at the various companies I worked for.

Why am I wasting my time, doing all of this work, for a cause I didn’t even really care about?

time is precious quot

What I didn’t realize at the time was that everything I did, I learned from. Every mistake you make (or don’t make) is a lesson. The time you spend at work doing something new (even if it doesn’t seem like it makes any sense), is going to teach you something that you can apply for yourself and your own business.

All of these experiences shaped you and have given you something that you can apply your career.

Even if it doesn’t feel like it now, these experiences that you’ve been through / are currently going through – are what will prepare you to be better in the future, and shape you in a positive way.


5. You have to take risks.

Well, if you’ve already made the jump – then you probably don’t need this advice.  Congratulations, you’ve quit your job and taken the huge leap into running your own business.  If you haven’t, and it scares the sh-t out of you, it’s okay, ’cause that’s normal.

surf honolua bay project inspo

Doing things that scare you – is a habit that I think everyone should have. Leaving a life built around a steady paycheck for the unknown is a big, big step that’s daunting and scary enough as it is.  If you don’t feel properly prepared, it’s even scarier.

But there is a trend in every success story, that screams at you when you start to compare all of them.

Successful people have taken risks to be where they are.  Every single one of them.

You absolutely have to do things that scare you, and I’ve learned that it doesn’t start or end with your decision to quit your job.  There will constantly be scary situations that come up, whether you’ve been doing it for 20 years, or 20 days.

The more you do things that scare you, the more you’ll learn.  If you fail, you’ve learned a lesson. If you succeed, well – you’ve succeeded. And none of this would have happened, if you hadn’t taken a risk.


6. Trust your gut and stay true to yourself. go your own way project inspo quote

Stop comparing yourself to other people.  Yes, you should learn from stories of those who have been successful, but there is a fine line between being inspired by someone’s journey and trying to mimic them.

Copying people will make you unoriginal.  Listening to others despite your gut telling you different will give you regrets.

At the end of the day, no one knows your business, your brand, or yourself better than you do.

So despite the distractions and the nay-sayers, keep going.  Keep learning.  Keep pushing.  And don’t give up.  Trust yourself and do not waiver when things get tough.


7. You’ll never stop learning.

Think you know it all? Well, you’re wrong.

I’m sure the music industry veterans didn’t anticipate a tech company turning the entire industry upside down.

I’ve learned that you absolutely have to open your mind to the possibility that you don’t know everything – so that you are open to learn, grow and adapt to changing situations.


8. You have to recognize your weaknesses.

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Believe it or not, you’re not the best at every single thing you think you are. It’s been tough for me specifically because I’m a perfectionist, and I never knew how to trust someone else with my work.  I always looked at my blog and my brand as my baby – no one knows it better than I do, and thus no one can do it better than I can.

I was wrong.

What helped me get out of this mentality was recognizing and accepting that my time is limited (duh) and often better spent doing the things that I’m actually really, really good at. 

Say you have 12 hours a day to dedicate to your company.  I used to try to split up my time across multiple projects I wanted to accomplish. What ended up happening, however – was that my perfectionist (cough, anal) side kicked in, and I’d be spending 8 hours awake trying to fix a line while attempting to code my website.

I literally just wasted 8 hours of my day to fixing something I could have hired someone else to do.

That same 8 hours could have been spent writing an article, sending out emails, out taking photographs, or editing video.

Learn to recognize your strengths, and more specifically – your weaknesses.  Let loose on the reigns a bit when you think about your company, so that you can look for those same weaknesses as strengths in other people.


9. Network your ass off.

Relationships are everything, and they will make you and make you.  Introduce yourself to people that you do not know.  But before you do, remember that first impressions hold a lot of weight.

If you do not have anything to show yet, work on that first.  Build up a portfolio, in any way that you can, so that instead of having to talk about what you’re doing or plan to do, you can show them.

This way, when you do introduce yourself to someone who could potentially be a mutually beneficial partner to your brand/company, you won’t be looked at as an amateur.

Building and maintaining relationships in any business is key to getting in the door, and staying successful.  People will hire you if they like you. People will remember you if they like you.

Someone told me once, “It’s who you know to get in, and what you know to stay in.”

Don’t be afraid to cold call, or send an email to introduce yourself.  And always be kind and humble. These two traits go farther than most think.


10. It won’t get easier, but it will always be absolutely worth it.

flying over medellin colombia

It won’t be easy, and the journey won’t be perfect. But everything that has happened, has happened specifically to prepare you for your future. Have faith in yourself, and trust that whatever is meant to be, will be. Keep pushing, put in the work, do your research, follow your passions and listen to your gut.

Remember that hard work always pays off.





Thank you so much for reading this post.  Do you have any questions or advice for our community?  Leave a comment for us below!


This post was sponsored + inspired by TurboTax.  All opinions are my own.


8 COMMENTS ON "10 Things I Learned After Quitting My Job To Work For Myself"


8 months 11 days ago

Great post, love all the advice.

8 months 9 days ago

This article has confirmed my desire to be a freelancer. Before this article, I had so many fears of failing. However, now I know that it’s normal to be afraid. You don’t succeed if you don’t take risks.

8 months 9 days ago

Thank you for this post! I’m about to make this leap to travel and freelance and it’s terrifying but so exciting at the same time!

8 months 8 days ago

Thanks Jinna for this post. It is very honest and forthright and I love that. It is really helpful for someone like me who may want to take the plunge into self-employment one day. 🙂


8 months 6 days ago

This is extremely inspiring and very practical – for instance I had never contemplated the tax issue.

Thanks for the post!

8 months 4 days ago

A really helpful and inspiring post. Thank you.

7 months 27 days ago

Jinna, I’m thankful Jo Barnes shared this. You rock and hit so many nails on the head. It’s all worth it, even the bumps, bruises and working until early morning. Looking forward to staying connected!

1 month 23 days ago

I wanna take the plunge but it’s so scary!