Jenna Rainey


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I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

Hey I'm Jenna!

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It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

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standing and deciding to hire a business coach

 Are You Ready to Hire A Business Coach?

Business Resources


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Are you ready to hire a business coach? This is something that I’ve had to ask myself time and time again throughout my entrepreneurial journey and today, I want to try and help you make the right decision for your unique business. 

While I really believe there is not a “one size fits all” answer for when to hire a business coach, I am going to walk you through some of my own experiences, and share the different stages we all go through in business to give you some context on how a business coach can help. Does that sound good? Great – let’s dive in.

business coach sitting outside looking at the camera

The Stages of Business and How a Business Coach Can Help

1. Ideation and Conceptualization

Whether you are starting a new business, launching a new project/product, or simply changing direction, it all starts with an idea. This is the dream phase, and it’s one of my favorites. However, transitioning from a great idea to a viable business concept can be daunting, so while in the early stages it can feel nerve-wracking to make a big investment into something like coaching, it can also be a GREAT time to invest to avoid waiting time or money because you’re too close to your idea to see any gaps or obstacles.

How a Business Coach Can Help: A coach can help you clarify your vision, validate your idea, and begin to structure a business model that aligns with your goals. They can often help you avoid shiny objects, and point out new perspectives you might miss when you’re seeing your idea with rose-colored glasses. If you can afford it, I think this is a GREAT time to seek professional coaching.

If you’re in the early stages of business, make sure to check out this post next where I talk about the stages you’ll go through when bringing your business from idea to fruition!

2. Planning and Launching

With a solid idea in place, the next stage that most of us will go through in business is the more detailed planning and launching phase. This phase might involve writing a business plan, figuring out logistics, and deciding on branding and marketing strategies. It’s also one of the most exciting phases because there’s a lot of ACTION happening!

How a Business Coach Can Help: If this is your first time, it’s likely not their first time (And if it is – it’s probably not the right coach for you!). Like I said, this is a time for ACTION. A business coach can help you create a plan to launch your new product or service out into the world and build momentum. They can also help you make the most of your newfound momentum and brainstorm ways you can ensure the delivery of your product or service is top-notch too!

3. Implementation and Growth

Once your business is up and running, the focus shifts to growth and scaling. This stage is about building a customer base, optimizing operations, and increasing revenue. In this stage, at least in my experience, there is less “new” happening, and more tiny tweaks and testing. It can feel less exciting, and that’s when business owners can start to get a little bored (and tempted to burn it all down and start again – we all know how antsy us creatives can get!). It can be hard to stay the course and really double down on what’s already working!

How a Business Coach Can Help: During this stage, a business coach can help you refine your marketing strategies, improve operational efficiencies, and implement systems for sustainable growth. They can both keep you focused AND assist you in identifying new opportunities that you might otherwise miss. If you are choosing to hire a business coach during this phase, I recommend looking for someone you can truly see yourself working with long-term (no “one-month” coaching here!).

I’ve made the decision to hire a business coach MANY times over the last decade

While I don’t believe it’s black and white when it comes to the right time to hire a business coach, I do want to say that I understand how hard the decision can be. I still vividly recall the nervousness I felt when investing $23,000 in my first mastermind. The financial commitment was enough to make my stomach drop, but something deep inside me knew it was the right step forward.

If you’ve followed me for a while, you know that I’ve learned time and time again to trust those inner nudges. Plus, this instinct was validated when, within just three months of signing the contract, I was able to triple my investment through the strategy and feedback I learned inside the program. You never really know the power hiring a business coach can be!

Behind-the-scenes of committing to a YEAR LONG mastermind 

If you’re still on the fence about whether or not to hire a business coach, let me just say this. Two years ago was my first time EVER committing to a YEAR-LONG mastermind. While the price tag was steep, I’ve also learned time and time again that at this stage in my business, growth takes time. I’m not in the “new” stage of business where I want to sprint and try a bunch of things and “hustle”. I have a solid foundation. At this point, I have a potential for HUGE growth everytime I do anything, but I want to make sure I’m being strategic in how I get there.

If you’re looking for mentorship or looking to hire a business coach, be realistic about the amount of time the transformation you want will require. There are a lot of “get rich quick” messages out there, but if you want to build a business that lasts, it takes time. A longer structure of support is going to help you make bigger moves in your business most of the time. 

artist painting and deciding whether or not to hire a business coach

Deciding to Hire a Business Coach

Listen, I firmly believe that a business coach can offer personalized guidance, accountability, and support that's hard to find elsewhere. Whether you're facing strategic challenges, getting in your head, looking to scale your business, or simply in need of a fresh perspective, a business coach can provide the support and outside perspective you need to achieve your goals. While I would be hard-pressed to say you “need” a business coach, I hope this post has made it clear that my coaching investments (which have racked up to multi-five figures!), have proved themselves worthwhile time and time again.

by Jenna Rainey 

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