7 Challenging Business Scenarios and How to Handle Them

Jenna Kutcher 

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January 19, 2022


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It’s 2022 — new year, new goals, maybe a new business? So many entrepreneurs (including us) are planners, but there’s really just one thing you can plan on as an entrepreneur — uncertainty. 

The challenges you might face as we dive into a whole new year of business are unpredictable. But even though we can’t predict what challenges this year may bring, we can prepare by learning from the challenges other entrepreneurs have faced before us. 

Kylie compiled a list of some of the most common challenging business scenarios facing entrepreneurs, and we’re going to play a game of “What Would Jenna Do?”

Disappointing a Client

When you let somebody down the first thing that I’ve learned is it’s not about you and your defensiveness. I think that a lot of times when people choose to hire a service provider, they’re hoping that that service provider has their best interest in mind and is going to do their best job for them. I would say most of the time we show up with those goals in mind, but I think a lot of times when we care so deeply about our work or when we’re so passionate about what we do, our first level of response is being reactionary and defensive.

I once worked with a couple as their engagement and wedding photographer, and when I returned their engagement photos, the bride was unhappy with how they came out. Really, it had nothing to do with the photos – she didn’t like how her makeup looked. But I had to figure out how to move forward with this client relationship. I decided to stand my ground and demonstrate that the photos were a true reflection of my quality of work, but if it wasn’t the right fit for this couple, I gave them an easy way out. The bride ultimately decided to continue working with me.

It comes down to setting expectations. When expectations aren’t set in any relationship, it leaves so much room to be disappointed or frustrated or feel like you’re getting forgotten. If you fail to set them in the first place, here’s your opportunity to learn moving forward how you can set them from the first time you say hello to a potential customer all the way through the experience. Really over communicate with that client what their options are, how you can remedy the situation, and the number one thing to do is repeat back their concerns, proving to them that you actually listened and heard them. 

Negative Reviews

I remember the first time I received a negative review. Does anyone ever forget their first one? It all started with a groom who decided to throw off a wedding day schedule with a round of golf that ran way late. The couple was in an actual fight on their wedding day and would barely stand next to each other for portraits. When I returned their gallery, they noticed the lack of photos of them together. This was part of their 1-star review. It was crushing, but what could I really do?

We’ve talked so much about discerning between feedback and just straight up criticism and understanding what can I do differently? What could I do better? And how can I remedy it? I ended up sending them back a portion of their payment versus arguing and holding on to every cent. 

One of the things I’ve learned is that you need to do whatever is necessary to protect your peace. If something is keeping you up at night or if something is consuming and bubbling over into your personal life, it’s not generally worth it. 

If you get a negative review and it’s public and you can respond to it, I highly encourage you to respond to it very thoughtfully and carefully. Have somebody else read your response before you post it. Again, reiterate what their problem was so that you prove that you understand what the issue was.

Competition and Copy-Cats

When I first started shifting into education, which was about three years into wedding photography, I was doing one-on-one mentor sessions. A local photographer signed up and in that session, I handed over the keys to the kingdom. I gave her my pricing guide and how I do my emails, how I walk through the year in my templates. Almost an entire year later I found out that she had literally just taken everything word for word and changed out her name and photos. Lesson learned! But thankfully, this did not hold me back from the education piece of my business.

When we see competition and when we obsess over it, when we let it really take away our peace, it’s usually due to a lack of confidence in what we’re putting out there. You’ve got to put your head down and the blinders on and do the work. 

There are absolutely scenarios and situations where you might need legal counsel, or you might need to go that next step, or you might need to send that email to bring the copying to their attention, but there are also circumstances where you’ve got to just let it go.

Want more advice on this topic? I’ve got a whole blog post for ya right here.

More from this Episode

From setting boundaries, hitting a slow season, and delegating tasks to someone else, this episode covers a range of challenging business scenarios that you may (read: will probably) encounter at some point in your entrepreneurial journey. Never fear! I know you can push through them, and hopefully my past run-ins with these tricky situations will shorten your own learning curve when you’re in the thick of it.

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  1. Crest says:

    There are really many factors when starting a business and you share it well.


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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