How to Know When it’s Time to Hire a Pro

You jump out of bed at 5 in the morning, make a pot of coffee, and start editing yesterday’s new product shots while the kids get ready. By lunch, you’ve dropped the kids off at school, answered emails, prepared the week’s Facebook posts, updated your ledger, solved a staff scheduling conflict, cleaned the shop bathroom, and worked the front desk for an hour.


I’ve always admired entrepreneurs like you. You work harder than anyone, tackling whatever needs to get done. You’re brave and unfazed by new challenges, trusting that you’ll figure things out as you go along. And you have an enthusiasm to learn like nobody else, jumping into every part of your business with the determination to do it all yourself.


The things I admire in small business owners are the same things that tend to get us into trouble, though. We run the risk of working too hard and taking on projects we can’t handle. We have a hard time letting go and handing the reigns over, even when its obvious we’ve gone as far as our skills can take us.


It makes sense. Your business is your livelihood. You’ve worked so hard to get it this far. You know its needs and quirks and goals better than anyone. And you have so much riding on it. But sometimes its better to bring in a professional to help. 


The first professional I hired to help me with Wild Olive Branding Studio was Jordan Walker, a business planner. It’s a decision I’m so glad I made! He brought so much value to the table and I wouldn’t have been able to make the progress I’ve made without his help. Here’s how I knew it was time to ask him for help: 


1. Doing it myself meant learning a whole new set of skills.

After I’d taken the time to move my ideas from my head and onto paper, I knew the next step was to put it all together into a business plan. Naturally, I opened up a new browser tab and Googled “business plan.” It didn’t take long for me to realize I was in over my head. I had no idea what a business plan should look like, much less how to even begin writing one.


There’s nothing wrong with tackling a project that requires you to learn some new skills, but if the amount of learning is overwhelming, it’s probably better to hire someone instead. I felt like I wouldn’t be able to do a decent job unless I went back to school and took some business classes. Since that wasn’t an option I wanted to explore at the time, I was better off asking for help.


2. Doing it myself would have delayed my progress.

I love an opportunity to learn something new, but I needed to get the ball rolling pronto. I had already taken more than a year’s break from working directly on my business and I couldn’t afford to take a few more months off to figure out how to put a business plan together.


Hiring a professional means you’re partnering with someone who knows what they’re doing and can get the job done much more quickly. My business planner knew what questions to ask me, what to research about my industry, and how to organize my jumbled thoughts into an organized plan. And he did it all in no time! It would have taken me months to do what he did in just a few short weeks. 


3. I would not have felt confident in the end product.

Even if I did my research, consumed a bunch of resources on business planning, and somehow got a pro to give me feedback, I would constantly be second-guessing and questioning the quality of my business plan. By doing this myself, I would be sacrificing the confidence and clarity I needed to move forward.   


It’s so important to feel confident in every part of your business. Confidence gives you the boldness to take brave steps forward. It energizes you to reach for bigger goals, to take smart risks, and to make good decisions for you and your business. Confidence is the last thing you want to sacrifice in a project. 


4. I did everything I could and still felt lost.

I wrote everything down. I took a great course that helped me organize my thoughts. I listened to business podcasts and read business blogs and tried to find business plan examples.  I tried to figure things out myself, and I felt even more lost than before.After all that, I still had no idea where to even begin. I needed someone to guide me through the process, to listen to me talk and talk and talk about my business, make sense of it all, and organize it into a neat business plan I could follow.


When you can’t find enough clarity on your own, find someone who can help. Someone on the outside can bring in fresh insights, new ideas, and an incredible amount of clarity to your business. They can guide you and give you clear next steps when you can’t figure out which way to go. 


Whether you need help with business planning, accounting, marketing, or branding (*hint hint*), hiring someone can be scary. It means letting someone in and trusting them with an important part of the business you’ve worked so hard to build. You don’t know for sure how things will go or if they will work out. But the risk is worth it because there is so much to gain by partnering with other professionals. We can’t do everything on our own. We need each other.

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