Self-Employment Tips: Our 2-Year Anniversary ~ Chicago Wedding Photographer

Well, here we are a little late on this post (our full-time anniversary was September 17th) – but it is here none-the-less! 😉 I have so much to say about this past year… that honestly – I’m not even sure where to start! It has been a lot of things – but overall I think the main word that comes to mind is BALANCED – even during crazy busy fall wedding season! Isn’t that exciting?! 🙂



I remember when I first went full-time back in September of 2011 (after busting my tail burning the candle at both ends on my business & at a very demanding full-time job at a law firm for 3 years prior) – I really thought going full-time would bring me so much freedom, time, and balance. But boy was I wrong! At the time it brought me a lot of pressure, a lot of late nights working, and a tough time in my marriage (because of the first two). But little did I realize at the time – that those things were ALL MY CHOICE and ALL MY FAULT.

Nothing frustrates me more than self-employed people complaining about how busy they are, or how tired they are. (And this was me for a LONG time… any of you who have been around for a while probably wanted to punch me back then, and by back then… I mean a few months ago probably. haha.) I glorified being busy. I wore it like a badge I’d earned on my Girl Scout vest (oh yes, I was a Girl Scout until I was 18 people! haha). I thought you weren’t self-employed unless you were proclaiming to the world how little sleep you had, how hard you worked, and how busy you were. For some reason I felt the need to show everybody I worked hard and that self-employment wasn’t what all those 9-5 people thought it was. It was HARD WORK.

Well, of course it is! But we don’t need to shout it from the mountain tops every 5 seconds! We also don’t need to run ourselves into the ground to prove to ourselves (and others) that we’re actually working. And we don’t need to work 24-7 to succeed. THERE IS ANOTHER WAY.

These were lessons hard-learned and lessons I am happy to have learned. I realized last year when I attended What If that my life was mine to live, and mine to construct! I could create the life I dreamed of! I could be more productive… I could be conscious about my scheduling… I could spend time with James… I could get up from my desk and move more… I could stop working at a reasonable hour… I could take days off. I could say NO to people!! (Oh was that a big lesson.) All of these things were possible – I just had to make the choice to change!

And so change I did.

I could ramble on forever and ever about what I changed, what I learned, and what things have made a big difference in my business this year – but instead – I’m just going to make a list! Because making lists is what I do best! 😉 So here we go! (This is a bit long – but I swear it is worthwhile!)


Lessons Learned in my 2nd Year of Full-Time Business:

1. Learn to say “NO”. (Or at the very least… “Not Now”)

It is hard, but I’ve turned some work away. We’ve turned weddings away that weren’t a good fit. We’ve turned shoots away for the same reason, or that we just didn’t have time for in our schedules. I’ve been more honest with friends, family, and colleagues about what I have time for and made an effort to only set dates when I have the time and mental space to fully be present with those I planned them with! (Why would I want to show up to dinner with a friend totally drained and wishing I wasn’t there…? How pointless is that?!) I’ve set dates moooonths in advance because I know I’m too busy at the moment to fit something in – but would love to catch up when things slow down. And so I set plans 2 months into the future with people, and that is A-OK.


2. Conscious Scheduling.

This goes along with number 1. It really is just being more conscious about when and what you put on your calendar! Feel free to say  “NO” to someone if you can’t make it work without being totally stressed out, or tell them “Not Now” if you’d love to but just don’t have time at the moment. Make rules for yourself about how much you can handle in a day, a week, a month and stick to them!


3. Days Off. 

Take days OFF. I don’t mean write it on your calendar and then end up working because you are behind and have an ‘extra day’. I mean TAKE DAYS OFF. I’ve done my best this year to mark 1 day a week “OFF” to sleep in, go out to brunch, relax with James, maybe clean the house (I like cleaning, it’s weird), make dinner (I also like cooking), hang out with family, with friends, or do something I ‘ve been wanting to try. Just living in the moment and enjoying life! It has been awesome!


4. Office Days. 

These first 5 points really all go together – but they are all KEY INGREDIENTS to making this work and to keeping my life balanced. I’ve realized that I need to have certain days of the week for Office Days (especially during wedding season). Unless it is very special circumstances – I try to have 3 days a week that I am home – with nothing on the calendar but a solid day of work in the office. I realized if I make plans to head out for shoots or meetings every night, then my brain is constantly watching the clock & worried about the things I scheduled later and I get NOTHING done. But if I have a solid day with nothing on the calendar except time in the office to catch-up on things – I am WAY more productive. I learned this early on and it has been a game-changer for me!


5. Out & About / Errand Days

This is the opposite of Office Days. Out & About / Errand Days are ones where I pack as much out-of-the-office stuff into a day as humanly possible, so I can take care of all of it in one day if possible. This makes the most sense for me for lots of reasons: …because Chicago has bad traffic… because I like to only have to shower and look nice enough to be seen in public occasionally (haha)… because I might as well go from one thing to the next while I’m already out of our neighborhood… and because I don’t get much done on days when I know have to be somewhere that afternoon. These days I spend the morning in the office catching up on emails, other odds & ends, and blogging for the next day. Then I spend the afternoon (for example) at the dentist, then right to an engagement session, followed by a meeting with potential clients (for example). I get showered, I map it out, and I’m on my way to tackle as much out of the office in one day as humanly possible.


Rules 1 through 5 Culminate to these Wedding Season Rules for Scheduling :

If we have one wedding booked for a weekend (on Saturday):
Friday must be an Office Day. I know myself too well at this point to ever think I could possibly schedule a shoot or errands before weddings. I get a bit anxious the day before weddings. I use that day to sleep in so I’m healthy & well-rested for the wedding. I prep our gear, print the timeline, and finish up last minute things that are left from the week that I need to accomplish. I have a low-key and early night in with James.

Sunday must be a Day Off. We are generally exhausted the day after weddings, so telling myself not to work that day isn’t usually that hard. Also – on Sundays the majority of the rest of the world has off so I’m not getting bombarded with emails from clients, or seeing other people working, then feeling guilt about not working, and then deciding to work. haha.

Monday is an Office Day. The day after we have a Day Off needs to be an Office Day so I can catch up on emails and get back into the swing of things. This also allows me to get a solid start on a week of work so I feel productive and positive.

Tuesday/Wednesday/Thursday are up for grabs for scheduling sessions, meetings, dates with friends, and errands. I only allow two of them to book up and whatever one is left is made an Office Day.

(And it starts over again with Friday being an Office Day.)

This means: At least 39 office hours per 12 shooting hours (if I book 2 sessions for my Out-of-Office days), 10 possible hours available for meetings/networking, and one full day off.


If we have two weddings booked for a weekend (on Saturday & Sunday):
Friday must be an Office Day. FOR SURE on double-header weekends without exceptions! I occasionally make exceptions for special circumstances if it is a one-wedding weekend, but never for double-headers. We need rest, we need to prep, and we need to be at ease before a crazy weekend of work!

Monday is a Day Off. (For the same reasons Sunday usually is – except the other people not working part. Clearly people are working but we are WAY too exhausted to care. haha)

Tuesday is an Office Day. (For the same reasons Mondays are usually Office Days – we have a LOT to catch up on after 2 solid days of weddings where we couldn’t check email, and a Day Off the following day.)

Wednesday is an Office Day. Because double-headers are double the work and I need more time in the office to recover from it, to upload cards, to cull, to blog, and everything else!

Thursday is up for grabs for scheduling things out of the office.

(And it starts over again with Friday being an Office Day.)

This means: At least 35 office hours per 18 shooting hours (if I book a session for the Out-of-Office day), 5 possible hours for meetings/networking, and one full day off.)


These rules have saved my life this wedding season!!! I have not worked myself ragged like last year! I am not running out every night for shoots or meetings or whatever! I am spending time with James! I have days at home to just Get. Work. Done. I have a night or two out to hang out with friends, or shoot a session, or network… and it feels balanced! But this didn’t just magically happen. I created rules for myself based on what I know I need to be happy and what I need to do to best serve our clients. I stuck to the rules… and it has been AMAZING.

(And YES I have the Packers’ schedule on my calendar… duh! 😉 haha)


6. Daily Essentials for Happiness.

I talked about these more in-depth in a post I did HERE. The original idea came from the amazing Natalie Norton who is such an inspiration to me, and I’m so blessed to call her a friend.

I started out really strict with my rules, but once I got used to having more balance in my Office Days I didn’t have to use the spreadsheet anymore to track it and am now better about my Daily Essentials on my own. For those of you that aren’t familiar with Daily Essentials for Happiness, basically they are daily rules (I suppose) that don’t allow me just to sit at the computer and work ALL DAY on my Office Days (or be on social media ALL DAY… haha). They are things I’ve realized that make me happy and balanced when working from home on a daily basis. This means that those days marked as “Office Days” are also used to have some time to myself – to meditate, to stretch, to walk with Chloe, to read, and more – on top of my regular work obligations. Each one of those things is equally as important as work that day and is vital to my productivity.


7. Outsourcing.

Oh my gosh – I feel like this is such a dirty word in the photography industry and I’ve struggled with whether or not to talk about this all wedding season!! But the truth is – a HUGE part of my balance and overall sanity this year is because I started to outsource all our weddings this wedding season!! (I still edit all engagement shoots & regular sessions.)

I found a company (Fotofafa) that I absolutely LOVE who makes a point to make sure our images look exactly as they would if we had edited them ourselves! They have fabulous customer service and I only have good things to say about them! I check their edits at the proofing stage, and I check them again (and make a couple changes if necessary) before sending them to clients. So I KNOW the quality is up to my standards.

Doing this has taken such a huge weight off my shoulders! It allows me to cull & blog our weddings, send them to edit (enjoy my life again), approve the sample edits, double check the final edits, and send them out to our clients for them to enjoy!  (If anyone is curious about the entire process from start to finish let me know and I may do a full blog post on it.)


8. Show yourself grace.

Be kind to yourself. Don’t expect yourself to do it all. (See #7) If some days you just aren’t mentally there and need to take a long lunch to have time to yourself, do it. If you are exhausted – allow yourself to sleep in. If you didn’t finish everything on your To-Do List that day … it’s OKAY. Be as kind to yourself as you are to others… allow yourself some leeway now and then.


9. Read/Play/Take lessons/Do anything – for the FUN of it.

This ties in with the Daily Essentials for Happiness and your Days OFF. Do things you enjoy that are NOT work-related. Expand your horizons. Try something new. Learn something different. You’ll be amazed how good it feels and how somehow in turn it inadvertently ends up being valid towards your business, and if it doesn’t – who cares – at least it was fun!


10. Set realistic expectations with your clients.

Let them know when to expect the photos. Let them know you have office hours by not replying after a certain time of night to emails (or include your office hours in your email signature!). It will make your life easier to let them know these things instead of having them need to email you to ask, or get frustrated that you didn’t reply immediately. Trust me.


11. Set email away messages.

This year I FINALLY started using away messages. If we’re gone all weekend shooting a wedding and sessions and plan to have a day off after – I put an away message up for those three days. Unless it is an emergency, I try not to reply until the date noted in the away message. This has given me such peace of mind while shooting and taking days off – I cannot even tell you!!!


12. Hold office hours. 

I don’t necessarily start at the exact same time every day (although most days I do start around 8:30/9am), but I try to end every day by 7pm. That way I can shower, make dinner, and have a few hours to decompress and spend with James before we start it all again. Of course on Out-of-Office days there is no such thing because I’m out shooting or at meetings late – but other days of the week I do my best to stick to this! Because while you think you’re being super productive staying up editing until 2am… let me tell you – you’re NOT. Because you’ll need to sleep in to make up for that, and then you’ll be so sick of having sat at the computer all night that there is no way you’re going to want to get anything done or sit at that computer the next day. (At least I don’t.) I’m way more productive if I’m balanced, I’ve learned.


Writing these down is as much a reminder for myself, as it is for you all to see! I try my best to stick to these rules – but again – like #8 says… I show myself some grace if I’m not 100% perfect and “on it” all the time. Sometimes I slip-up… sometimes I work later than I intended… sometimes I email past 7pm… but that doesn’t mean the next day I can’t be better. Overall I’ve learned that being positive is the best thing for me, my business, and my productivity.

Of course I feel like I do still have moments of fear, frustration, worry, and doubts… but overall I’m much better at trusting that things are moving in the right direction. I believe this is where I’m meant to be in my life and what I’m meant to be doing with James by my side. I trust that if we continue to put our full hearts into it it will work out. (Even though writing that just now feels like I’m jinxing myself… haha. Stupid superstitions!)

Looking back, this past year has been a really amazing transformation for me. I can’t believe how far we’ve come, and even just personally – how far I’ve come towards being the more joyful, kind, calm, and present person I want to be. Of course there is always room to learn and improve… but at least I’m on the path and I’m walking in the right direction. And that’s something.



(I couldn’t help but use these photos again today – they just felt so appropriate to wrap this up!) 🙂


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Christy & James are Chicago based but happily travel anywhere in the world that beautiful love stories take them!