I finally quit my job. Well, kind of...

This isn't another post like the ones we see all the time. The classic: "I was so sick of the 9-5 grind that I'm just quitting and packing up my dad's Jeep to hit the road, all the while crossing my fingers  that my freelance career picks up and I gain a million Instagram followers and all the coolest brands suddenly are reaching out to work with me." Or even better, "I think I'm just going to drop out of college and travel, and since I have all these Instagram followers, I've pretty much got it all figured out." 


Side note: I'm applying these thoughts mainly to those thinking about pursuing adventure and travel photography - not wedding, engagement, etc., for that's an entirely different field.


I'm all for dropping everything and taking risks. I've absolutely taken my fair share, but when I see people talking about doing things like stated above, it really makes me wonder how far into the future they're thinking. Following your dreams is one thing, but compromising your future is another altogether. I could go on and on about this subject, but I'll save that for a future post. 

Through this process, I hope to encourage you guys that it is possible to pursue freelance travel and photo work, all while making legitimate investments into your future. Investments that companies in 5, 10, or 15 years will actually want to hire you for once Instagram is dead and nobody cares that you had 500k followers on an irrelevant platform.

Yes, there's tons of people out there who are doing incredible things with their freelance career after dropping out of school or a job, but they also put in hundreds of hours to get to a point where they could legitimately pursue clients and make ends meet. This is incredible to see happen, but it didn't happen overnight, as so many of us dream that it would. Nothing has been better than seeing my friends who have slaved over their passions finally catch their breaks. It's really awesome.

This post is more for those who haven't done the work, don't know what the next steps are, or even what they 100% want to do. That was me just two years ago, and I'm still figuring it all out.


So how did I get to this point where I'm quitting my full-time agency job?

This time a year ago, my friend Kyle and I were toying around with hitting the road for a few months to make a movie. It was just an idea at the time, and it turns out forsaking this project was the best thing that could have happened to me. I truthfully wasn't ready for it, and there's no way it would have turned out how it needed to in order to be successful.  

The year before that was spent traveling, getting better at photography, and figuring out how I wanted to use it in a professional sense. It was during this time that I uncovered my passions for storytelling and digital marketing, and I was desperately looking for a way that I could use it to make ends meet. I never thought I'd be able to do it on a freelance basis, but I just couldn't figure out what the next steps were.

The years before that were spent at college, where I studied business and communications, which turned out to be vitally important to running my own business, as well as having a degree I could fall back on if things ever went south. A degree isn't everything - in fact, it's not a guarantee to success whatsoever. But, it certainly doesn't hurt. And college can be a fantastic place to learn, grow, and mature as an individual, as well as build a network of people that care about you and could help you in the future. All of these can be extremely important things in being successful down the road. And the ability to apply these skills to your own photography business is incredible valuable.

So flash forward to today, the first day on my own as a freelancer.

Why did I make this decision?

Over the past year, I was able to learn firsthand about how an agency works, which meant everything like pre-production, content creation, finalizing deliverables, and financials. These were something I had direct exposure to. It completely redefined how I dealt with personal clients, and gave me the knowledge and insight into how running a media company works, which is essentially a collective of freelancers working together on bigger projects. This knowledge is 1000% transferrable to doing freelance photo and video work, and has given me the ability and confidence to actually pursue clients like never before. 

Being around likeminded people always keeps the creative flow going, and it's even better when they are guys who have been in the industry for over 20 years. Just that exposure alone was worth working an office job.

Keep in mind, you can always learn these skills on your own. The internet has been crucial in my development as a professional. But, the ability to learn, while getting paid, is one I can't recommend highly enough. While I wasn't always using photography on something I was super passionate about, the learning process helped to set me up so that I could be successful with the things I'm passionate about. 

During this time, I traveled when I could and used weekends to get out and shoot. This is certainly not the worst thing in the world if you live somewhere that has cool spots just a few hours from you. I unfortunately don't, which only made the past year tougher.

What advice do I have for others thinking about quitting their jobs, dropping out of school, etc.?

I hope to dive deeper into this in the future, but my ultimate advice would be to carefully plan your next steps and ask yourself the tough questions. Is dropping out going to to really let you have more time for legitimate work and improving your skills, or do you just want to travel? There's a huge difference there.

I'd also look 5 years down the road and ask yourself where do you want to be, what do you want to be doing, and how can you make that happen for yourself. Planning is incredibly vital to life. 

I'd also give legitimate thought to the Instagram game, and asking yourself what you'd do if it disappeared tomorrow. Would you even shoot or produce content? Would you have skills to work at a job? What kind of job would you want to work? Don't put all your eggs in one basket - this can be incredibly dangerous. 

What's next for me?

Like I mentioned, this decision was extremely well thought out. In fact, I've been planning how to make this step for over 4 months now. I wouldn't have done it without being able to line up enough clients and legitimate work for the next several months. And I wouldn't have been able to do that if I didn't grow my business, photography, and video skills over the last year with my agency.

The next few months will be filled with travel, freelance photo and video work, and then a career transition to another full-time job this fall, which I couldn't be more excited about. 


The journey will certainly be challenging, but I couldn't be more excited for it. I hope to document it all, and give as much advice and guidance to people who need it along the way. 

As always, feel free to reach out if there are any questions I can answer, or advice I can give.

Thanks for following along. 

- HB