Taking a Leap


Kelly Rehnberg/
Community Voices

Kelly is a Real Life community member who is here to share the top 10 things she prioritized to successfully quit her job and jump full time into photography.

Earlier this year, I resigned from teaching middle school music to pursue my wedding photography business full-time. I am someone who enjoys playing it safe, so believe me when I tell you that this decision was difficult for me. So often, we hear phrases such as "chase your dreams" or "just go for it" when people encourage us to pursue our passions on a full-time basis. I absolutely believe in chasing your dreams, but I've watched many people make this huge decision without adequate planning.

I have been juggling photography and full-time teaching for three years, but in total, photography has been an 8+ year journey. Several years ago, I was fresh out of a relationship filled with domestic violence. I found myself living alone for the first time in my life, had basically nothing in my bank account, and lived in a small apartment. I share this with you, because I want you to know that this was my reality only 8 short years ago. I’m not someone special or lucky. I was just another person with a camera, taking photos of my dog and looking for a passion to heal my soul. 

During this time in my life, I dabbled in photography with a Canon Rebel t1i and kit lenses. I officially launched my business in 2013 with a Facebook page, a website, and way too much newbie confidence. I didn't think about photography as a full-time career until about a year ago. I simply assumed it would be a very lucrative side hustle, but when my business began bursting at the seams, I was forced to begin thinking about my future.

Thinking about completely quitting my teaching job seemed idiotic. After all, it's what I went to college for and I still have student loans to prove it. At any rate, I knew I couldn't "just quit" my teaching job, so I began ramping up my photography business to see what I could do. To feel at least 99% ok about my decision, I set a goal to replace my current income while still teaching and that's exactly what I did last year. 


Here are my top 10 steps and considerations I took before (and during) this transition (*expert tip – this was not easy)

1. Seeing is believing
Track your expenses and your income - ALL OF IT

You MUST have a visual way to track your numbers before even considering quitting a day-job. Also, have a separate account for business to help streamline this process. You will be shocked how much you spend on your business even when you *think* you have all the gear you could ever need. The hard truth is that there is always gear to buy or something new to spend money on in this field. I was so shocked to see the total of my business expenses.


2. Uncle Sam needs to be your pal
Find a reliable accountant, pay your taxes (cry) and learn your local sales tax laws (cry some more)

This part of the business truly has had me wanting to bash my head into a wall. Not all accountants are familiar with photography tax laws and even still, you NEED to know your tax laws inside and out (it might take you awhile to find a good accountant. Ask for recommendations from other local photographers). So many people start out and think: "wow this is great! I just made XXX for one wedding day!" but when it comes down to it, so much of that money will be going to taxes or back into your business.


3. Don't let Uncle Bob break his face on your light stand
AKA . . . Get insurance

I’m still shocked at how many people I meet who admit they still aren’t insured. Insurance isn't a hard thing to get set up (or as expensive) as people think. I started out with adding this on to the same company that my home is insured with, but there are several options out there. You must protect yourself from the potential Uncle Bob that breaks his jaw tripping over your light-stand or the drunk groomsman that spills liquor on your new lens. Always remember you are only one crazy person away from losing your entire business.


4. Breaking your legs, dying and other unsexy discussion
AKA . . . Health insurance/life insurance/retirement

If there was anything that was weighing on my decision to quit teaching, it was health care/benefits. I'm one of those people that frequently imagine myself plummeting down the stairs, breaking both of my legs, and catching on fire, so I cannot imagine NOT having health insurance. Luckily, this year my husband's company began offering healthcare, but we will be paying much more per month than ever before. Plus, we had to research options for life insurance, retirement, etc. (all things I previously had set up or provided at low rates). 


5. Another (unsexy) consideration

Be real with yourself. How much debt do you have? If your business took a hit or you have a rough year, will you be ok? All things considered, I could have quit teaching last year, but hanging on another school year has been the best decision I have made. We have spent the last year paying off nearly all of our debt (minus our car/house).

6. The safety net
Saving $$$

One of the best decisions we’ve made during this process is NOT SPENDING the photography funds. It can be tempting to "dip into the photography funds" but I mean it when I say I've tried hard not to do this often. If we were constantly spending the photography money it would have been giving us a false sense of security. I now have almost a year’s worth of income saved, which I’m still in disbelief about.


7. The "what if things blow up in your face" tip
Back up plans

I like safety nets and you should too! What are your other skills? Are you leaving a job that was hard to get in the first place or could you return if needed? Besides photography I can teach private music lessons or substitute teach if I run into problems, but I know I can go back to teaching too. 


8. Can you still 'drop it like it's hot?'
Physical and mental health

How does that look for you? For me, I have not been the healthiest person (mentally or physically) since I've been working towards this goal. The combination of stress, chips/salsa binges and late nights finally caught up with me earlier this year. Self-employment means taking care of your physical and mental wellbeing, because you will no longer have sick-days or paid time off. I've worked hard to clean up my diet, (with fewer chips and salsa binges), and have begun weight lifting to avoid the dreaded wedding hangovers. Also, we all know how vital our mental health is. (I could write an entirely separate blog just on maintaining mental health while running a business).


9. Friend or foe?
How is your relationship with other local photographers? 

Having the support of your local photographer friends is incredibly vital. Join and actively participate in your local photography Facebook groups. Stay guarded, but be a leader. Stay out of drama, and choose your photographer friends wisely. Even as a newbie, I created a local group to connect with other wedding photographers and second shooters. It's a small group, but my community lacked an inclusive group that was strictly professional wedding photographers. I've met and connected with so many people by creating and admin-ing this group. We share advice, referrals, borrow gear, etc., and I know I have several new friends that would have my back in an instant.


10. Can they handle it? Can you?
The support of your friends and family - And the time factor

For most people, this transition must happen gradually and at some point you will be juggling two full-time jobs before you can leap. I'm warning you, you will have NO LIFE and most people will NOT understand why you are doing this (*insert judgmental people). Your house will be total chaos, people will get offended, and many others will tell you to stop working so much. Even if you have a free night you will be sleeping, refusing to leave the house and/or having deep conversations with your dog. No matter how strong your marriage/relationship is it will put a large strain on it. Your partner absolutely needs to be on board with you. I'm 100% convinced that if my husband wasn't the crazy-determined-supportive person that he is, we'd probably be divorced or killing each other by now. 




At the end of the day, the process is very uncomfortable and will (mentally) test you more than you can imagine. I was terrified the day I resigned from my teaching position, but it feels amazing to take a risk like this in my life. I have put my entire heart and soul into making this dream a reality and I have many goals that I'd like to accomplish in the next year. I want to live a life that I love and that I'm proud of. Now I know that no matter what happens, I will be able to look back without wishing I had 'just gone for it.'

The best advice I can give you is to work hard and believe you can do it. I'm a huge believer in putting out energy into the universe that you want to get back. If you believe it, you can do it.

So get out there and rock it!


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Blog Image by Katelyn Malo Photography

Mary Moore