3 Important Lessons I Learned From Starting a Photography Business TWICE

In 2009 I found myself a divorced single mother of two little boys. I hadn’t planned to ever be there - my parents had divorced when I was very young and my dad had been married enough times that you needed two hands to count them all.

I never wanted to put my kids through what I went through as a kid, and yet, I found myself a divorced single mother anyway.

I wanted to embrace that time in my life as a lesson, one that I would never forget, and learn from it and become a better person. Part of what came out of that time was me deciding that if I was already at what felt to me like rock bottom - broke, brokenhearted, emotionally devasted, struggling to make ends meet - that I might as well figure out how to do life on my own terms.

I went through a lot of introspection, and what I found was that I loved photography and thought I’d like to give it shot. So, one night, with only a few bucks left in my bank account, I opened a new credit card with a small balance and immediately maxed it out on a Nikon D90 with a 18-55mm kit lens on EBay.

And with that, my business was started (the first time).

It was a S T R U G G L E to get started at first. I wasn’t sure what to do, so I spent a lot of my time Googling, searching, trying to follow the advice I could find. I messed up SO much and had to re-do SO many things - business names, logos, websites - but I kept studying, kept practicing, and my photography, editing, and business got better and better.

Eventually I got remarried and now had 5 kids…and the business started to feel like it didn’t fit anymore. I had grown it so much that I was working non-stop, and in the height of my busiest season, sometimes worked 80 hour weeks. I was missing soccer games, band concerts, musicals…

And then my stepdaughter entered her Senior year of high school.

While I was so proud of the business I’d built, it just felt like it had become another version of what I never wanted to be - a slave to work. I was missing so much of my childrens’ lives - and that was what I had started the business for in the first place. I was missing it, and my time with them wouldn’t last forever. In fact, with her, it was almost over. We really only had one year left before she went away to college.

I decided - it was time to put the camera down.

Fast forward 6 years: all the kids were out of school and we were desperately searching for a wedding photographer for my stepdaughter. We finally found someone that seemed reliable and like they had their shit together (and she did, she was amazing!) but I had the thought that it should not be that hard! I know there were courses out here for all sorts of marketing and business stuff! Where was the help for the new photographers?!?! Why was it like this?

I’d already been itching to get back to doing something creative again, and had even opened up slots that fall for family photos and had several sessions for the first time in years.

So, after giving it a lot of thought, I decided it was time to pick the camera back up and started a photography business (the second time) and also, help others with all the business and marketing knowlege I’d built over 16 years. Again, it was the only decision that felt right at that time.

This time, though, I didn’t randomly buy a camera, I didn’t need to spend hours and hours and hours searching Google on what to do or struggle so much. I’d had years to think about how I’d do it differently, how I’d simplify, how I’d make it a more fun and easy experience for my clients, and years of building my own knowledge and experience. I knew I could be a great photographer, capturing memories for families, helping entrepreneurs build a portfolio of images that amplified their brand, and I could also teach others how to do that as well, in their own unique way.

So here are top 3 the lessons I learned that I applied the second time that made everything more fun, more efficient, and more profitable!

Lesson 1: You don’t have to do anything that doesn’t feel good to you!

Look, there are a lot of experts out there giving out business advice about things that work and things that don’t and as much as I’ve studied business and marketing, I can tell you this: what works for others might not even work for you. So you might as well just choose to build processes and work with the channels that excite you and light you up!

Some swear by Instagram. Some swear by Google Ads. Some swear by their super amazing funnel and if you don’t have one, well, “you’re just leaving money on the table”… it’s 2025, we’ve heard it all, we’ve seen it all, and I’ve tried it all (well probably not all, but because I worked in marketing, I’ve tried a LOT of things!)

Here’s the truth - I’ve seen people make astonishing amounts of money in some of the most bizarre circumstances. The keystone to the entire business ecosystem is to work with your strengths and what feels good and makes you happy, and to avoid at all costs doing things that make you feel gross.

If you love Insta, build there. If you love email lists and writing blogs, definitely do that. If you hate Facebook, feel free to delete the app off your phone. Life is short and complicated enough without making it miserable with forcing yourself to do things you don’t like doing, just because you think you “have” to for your business to be successful.

It can be successful in so many ways. Choose to set it up in ways that feel good to you, and if you’re feeling overwhelmed and don’t know what your options are, we can have a Zoom coffee chat about it and I can help. Or take this self-assessment to get some clarity on what’s working and what’s not.

Lesson 2: Embrace the “SLOW BURN”- You don’t need EVERY SINGLE SHINY THING Right Now

I really wish someone had told me that I would get super excited about tech - both hardware, like cameras and lenses, and software, like gallery sites and automation services - as easily as I do and that the best thing I could do for myself as a new photographer is to learn to filter!

Filter what, exactly? Filter what I really needed, and focus my limited time, energy, and money on the things that are the most important and will move the needle the most.

This requires a lot of deep breaths and patience, things I already don’t have a firm grip on, and a willingess to be practical first and splurgey second. I wasted a TON of money the first time I started my business on things I thought I needed wanted that I ended up not even using!

When I started my business the second time, I had a small list of things that I knew would make the biggest impact for my refreshed business right away:

  • a new camera and lens

  • an updated gallery site

  • integrated studio tools (like online contracts)

This allowed me to save some money for advertising later when the season really gets going, and allowed me to focus my time on the marketing that really felt right for me and how I wanted to work within this new iteration of my business. I wanted nothing to feel overwhelming or gross, or worse, like I’d wasted money on it.

So I went slow. I respected the journey.

If you’re just starting out, you can start with free trials, rent out equipment to test drive them before you buy, all sorts of things! Be careful about your investment - protect yourself from yourself - your excitement really can run away with you when everything is new and shiny! And give Time some space. It takes time to become experienced, so allow yourself to enjoy the journey. You’ll get there… one step at a time.

Lesson 3: NOW - right at the start - is the time to build your confidence and self-esteem, so you can have healthy boundaries and set healthy prices

The right time is not in 3 years, when you’re broke, burnt out, hate the portfolio you’ve built because you went against yourself just to make whatever money you could.

The time is NOW.

If you’ve not invested in yourself, if you’ve not done the inner work that will allow you to price your services and products where they need to be so you make money, do that now. You don’t have to wait to start, but do those first steps, and this inner work, in tandem. THIS IS SO IMPORTANT: photography is an emotional business, but it’s still a business!

The reality of this is that you’re going to be faced with people, all the time, who tell you that your services “cost an arm and a leg” and who don’t understand the value, or the time commitment, that is required to run a photography business.

They won’t get it that you’ll feel like they’re saying that YOU aren’t worth it… even though it will feel that way.

So the most important thing you can do in the beginning is a two-fold process: work on yourself, and set your business up with supportive pricing and healthy boundaries.

This means contracts/agreements/documents that outline your services clearly - what you will and won’t do - and sets appropriate expectations.

This means exercises that build and stregnthen your spirit, your own sense of worth, your confidence, and your grit and perseverance.

The sooner you get good at saying no - with respect and love - the faster your business will grow!

ALSO READ: Photography Business Pricing Strategies (and why In-Person Sales DIDN’T work for me!)

BONUS: I believe in you!

Photography is an emotional, worthy profession and I am so grateful for having this business in my life. It changed everything for me as a single mother, and it’s changing everything for me again as an empty-nester. Even deeper, aligning it with my human design took it to a whole new level and now I get to run a business that I am so deeply proud of, fulfilled by, and get to experience a deep sense of purpose.

And even more than that - YOU CAN, TOO.

Photography, or any kind of creative business - whatever you’re doing! - is 100% WORTH IT. If you need help, I got you. If you need information, that is here and everywhere on the big, wide and wild internet. If you need photos to tell the story, or want to get deeper into your human design, call me!

But the truth is… you can do this. If I can do this - me, I’m nobody, really! - then YOU most certainly can.

Trust yourself. You got this.


WAIT! I have something for you!

FREE GUIDE - 10 Steps to Pricing Your Photography

Still not sure how to price your photography packages and services? Not sure when to raise your prices?


Sam Sherwood

Sam is a photographer, writer, and ecologist. Drawn to nature from a young age and fascinated by the interconnectedness of life, in 2009 she started a photography business and in 2019 she closed it to focus on her family and change careers to focus on the environment. Sam relaunched her business in 2025, and now shares mentorship for clients and photographers along with ecologically-centered research, philosophy, self-development, and stories that explore the rich beauty and physiological link of the human/nature relationship.

https://www.samanthasherwood.com
Previous
Previous

5 Ways to Align Your Business with Your Human Design Profile: A Creative Entrepreneur's Guide to Heart-Led Success

Next
Next

Photography Business Pricing Strategies (and why In-Person Sales DIDN’T work for me!)