Should you work with a business coach?

When is it time to work with a business coach?

Several people have asked this question lately—and I have opinions!

I have been working with Ilise Benun for five years. There’s something about having somebody to share your progress with on a regular basis that’s monumental in helping you get stuff DONE. Yes, it was slow-going and difficult at times, but looking back now, I can say with 100% certainty, it was worth it. The idea of working with a coach had always been on my radar, but one day five years ago, I was just ready…and maybe you’re ready too.

It’s time to work with a business coach if:

  1. You’re in stranded in Stuck City, USA. If you have ideas but you’re not making any progress on them (despite your constant declarations to “finally get this done!”)—a coach can be the kick-in-the-butt you need.
  2. You’re making a shift (or you need to). Want new, better clients or different types of work? You might need a coach if your business is changing or it’s time to re-think it. (This is why I reached out to Ilise. I was working for a client I didn’t like and knew I needed to transition, but wasn’t sure how.)
  3. You’re just getting started (and aren’t broke). If you want to skip the part where you struggle and figure it out yourself for a while, the right coach will help you get there quicker and stronger.
  4. The idea keeps nagging at you. If you keep thinking, “I could be doing so much better if I had someone to keep me on track,” or “I wish I had someone to help me get clear on this,” it might be time for the outside influence of a coach.

But before you jump into working with a business coach, here are a few things to consider:

  • It’s an investment. Coaching costs money. Look at it as an investment into your business. Yes, you will make up the money in projects you wouldn’t have gotten—but it’s also an investment in yourself which you can’t put a put a monetary ROI on.
  • It’s not a magic pill. You don’t work for a month and bam, your business is better. It was very slow for me. I used to apologize every week at the amount I wasn’t getting done. But I’ve stopped apologizing. I’ve gotten a lot done in these years. But seeing results takes time.
  • You will feel crappy, and you will feel awesome. Coaching works for lots of reasons. One is because if you’re not making any progress, you will dread those phone calls/meetings (so you’ll do the work because you don’t want to be a slacker). Another is because it often pushes you outside of your comfort zone. It can be emotional! Just like web design is like therapy—so is coaching!

What about the results? Looking back at where I was five years ago, I can say the results of coaching are pretty drastic. Today I have CLARITY about my business. I know my ideal client. I know my value and what to charge. Instead of feeling one step behind, I feel like I’m proactive. It feels awesome to be reaching goals and setting new ones.

Thinking about a business coach? Find the right fit.

Most coaches will offer a free conversation so you can see if you mesh. That’s really important. Ilise had been on my radar because she specialized in working with people just like me. When we talked, I knew her style would fit mine. She had the right amount of guidance, accountability, niceness and toughness to keep me on track.

Not ready for a business coach? Get accountable somehow.

An accountability group is different than working with a one-on-one coach—but it can be beneficial to connect with your peers. I’ve been a member of the Creatives Roundtable for 4+ years. We all come together, share our challenges and successes, learn from each other, and keep each other on track.

Have any coaching success stories to share? Please share in the comments!

Are you concerned about critical areas that can make or break your creative biz such as contracts, money matters, and qualifying prospects? My Client Onboarding Toolkit is a simple, 4-step digital course that walks you through my time-tested process for onboarding clients. Jam-packed with advice, tools, and templates designed for creative professionals, it’ll save you time, stress and frustration while making you look like the creative rockstar you are. You’ll convert prospects into paying clients with more clarity, sanity, and confidence than ever before. Learn more »

About Jill Anderson

Hi, I’m Jill, a WordPress WordPress designer/developer who partners with talented designers, copywriters, and agencies on their websites, and their client’s sites. I’m passionate about crafting beautiful and innovative WordPress websites focused on clear positioning and positive user experiences. Get my free report, Get Your Website Done: 12 Actionable Steps for Designers, and check out my Client Onboarding Toolkit, a simple 4-step digital course for converting prospects into a paying clients.


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