Leah O'Connell

for photographers

Questions to ask yourself when you feel stuck in your photography business

I'm Leah!

I’m obsessed with stories of family, creativity, and simple joys.  A nostalgia nerd, educator, wife, and mom of 3, I believe life’s most fun when you’re dreaming big and having kitchen dance parties. 

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There are always so many moving pieces to building a photography business, so it’s easy to get stuck. As family photographers, we often start scrappy – we have a passion and we want to make a living with it, so we pull bits and pieces together for this puzzle of meaning and capturing, but also… how to work well with clients, create a smooth backend process, market, sell, design… wow.

In time, we can look back and realize we’ve built something we didn’t really intend to build, and the bricks are covered in cracks.

Building anything can be overwhelming at the beginning.

A poem starts with a blank page.

A home starts with plot of dirt.

A sculpture starts with a hunk of clay.

How do you move forward in creating something helpful, beautiful, or important when you don’t know what the next step is supposed to be.

When there’s no “right way,” no floorplan?

The following questions have given me clarity to take action when I’ve felt stuck in my photography business, so no matter where you are in your journey, I hope they’ll provide a good starting point for you, too.

Questions to ask yourself when you feel stuck in your photography business

1. Am I making this harder than it needs to be?

Raise your hand if you’re a spinner? Like as in, you take one thought and project a million possibilities, assumptions, other ideas, and to-do’s upon it immediately trippling that thought into a tsunami of projects, plans, and what-if’s. This is probably my biggest hurdle.

By asking this question – am I making this harder than it needs to be? – I’m often able to recenter myself into examining the problem or idea from a thoughtful place, rather than a frantic one.

2. What needs done now, next, or later?

When projects feel overwhelming, it’s helpful to examine the pieces in chunks and determine the MVP – the most viable product. What parts are urgent, what parts can come next once those are done, and what pieces are non-crucial (or even just can’t be considered until A and B are complete?). YOU ARE HUMAN so be honest with yourself.

Not everything is an emergency, calm down.

3. What’s the real problem here?

When you look at a problem closely, you’ll often find that the real issue is about 2-3 levels deeper than the surface one you think you’re trying to solve.

If you skip this question, you risk spending a lot of time making something or working on something that won’t really address the real crack.

A quick example:

Say you’re not getting many leads for your work so you might think – “I gotta be more active on social media!”

You start spending tons of time making posts that show your work and call people to action.

BUT REALLY, if you stepped back to examine the problem, you would have examined your analytics to see where your existing traffic was coming from, first. You would have discovered that you’re actually getting a ton of people to your website via google —they’re just not reaching out.

This shows you the deeper problem – it’s not that you’re not getting leads, but that the leads are already there and you’re just not capturing them.

Now, your next best steps are narrowed tremendously – this is a communication issue! You need to refine your messaging and the presentation of it and your work on your website where people are already connecting with you! Social media might help, too, but only if your messaging is clear, right? So message, copy, and clarity need to be step one.

You know you need to dig into how you can do that most effectively first. Do you need a website review? To hire a copywriter? To uplevel your website platform from a clunky old interface to a more moder design?

Yes, there are decisions that flow from every path of your discovery, but you can have confidence that you’re walking in a purposeful direction.

By jumping to the solution of posting more to social media without thinking deeper to the real problem, you’re missing a whole market of people who are way warmer leads and actually wasting a lot of time.

4. Is there any harm that can come from doing x vs y first?

When there are many cracks in my puzzle or things I could be working, reverse psychology sometimes helps to choose what comes first. If I work on x, will y suffer?

If you’re stuck on knowing that building out a CRM tool will help you manage client workflows, bookings, etc. for your mini sessions but there are SO. MANY. PIECES so you just keep putting it off…. will it hurt if you start with email templates vs. booking proposals? Both need done, so…

Is there any harm in just starting somewhere? NOT REALLY.

Pick a pain point and dig in. Even if you have to go back and adjust it later because of new information, you’ll be more familiar with the platform and knowledgeable about how to adjust more swiftly in the future.

5. A year from now, will I thank myself for doing _____?

When you think of what you want your business to look like 1 year down the road, and how you want to feel, will taking this step be an important piece of getting you there?

How will you feel if you don’t and you’re in exactly this same position?

Will future you be cursing at past you for not doing taking this action? Or will she/he thank you?

Sometimes decisions are as simple as yes or no. If it’s yes, then you know you need to make some moves.

6. What it the “yes” to “no” exchange?

Saying ‘yes’ to one project or idea always means saying ‘no’ to something else.

For example, you can’t decide to add a 10+ hour project to your schedule with a one 1 week deadline without knowing where you’re going to put those 10 hours of work.

Are you going to add them to the start of your day by waking up early?

Will you need to hire a sitter for 1-2 days for solid focus?

Do you need to be more realistic about the timeline?!

Can you outsource?!

Maybe you need to let some things go around the house for the week and just be okay with it in the name of your ‘yes?’

BE HONEST WITH YOURSELF and you will ease guilt and pressure tremendously by setting yourself up for clear goals and a challenging but doable framework for them.

Questions and reflection are vital to building a business you’re happy in and with.

If you barrel ahead full-steam without looking around, you’ll find yourself in a home that’s unstable and decorated terribly for your style.

What are you trading in order to continue balancing on a shaky foundation? What problems are you saying —“that tool is too confusing, so I’ll keep doing it the long way because it’s easier.”

Only it’s not easier. It only seems easier now because it’s familiar.

Walking was hard before it was familiar. Now look at you!

Marie Forleo has a famous phrase – “everything is figure-outable” – and this is so true, especially when you can predict the end goal as peace, flexibility, freedom, and joy.

It’s worth figuring out, taking that baby step, and taking just one bite in order to get you closer.

These are just 6 questions to ask yourself when you feel stuck in your photography business to help you find your next best ‘yes’ one step at a time.

You might also like:

5 Essential tools for running my photography business

3 Games for directing outdoor family sessions

If you’d like some extra one-on-one help to untangle your workflows and align your brand, reach out and schedule a mentoring call with me! I also have some free resources here to get you started- let’s work together!

Hi, I'm Leah.
Family photographer, writer, educator.

I’m  one of the first to meet your newborn baby, the one who won't judge your clothes baskets and unmade beds, and the one who can capture the way your husband looks at you with a twinkle in his eye after 12 years of marriage. I believe in honoring people and telling stories.

I believe art has the power to light up the world in dark places, starting at home.