Why Hiring a Business Coach is TOTALLY Worth the Money

I recently started doing business coaching with one of my personal heroes, Pamela Slim. I used to read Pam’s blog, Escape from Cubicle Nation, back in 2009 when I was trying to start freelancing and was stuck in a cubicle all day and wasn’t sure how to take the leap from the corporate world to solo-preneurship. I didn’t have any local role models; I didn’t know anyone in my own city who did what I wanted to do for a living. So I lived vicariously through Internet heroes like Pamela Slim, who showed me the possibilities of a magical world of people on the Internet, working from home on their own terms while wearing pajamas, and making a good living at it. That’s all I wanted, early on – I just wanted to work from home and be with my family. I had modest goals and simple needs.

Over the years, I’ve gone from those modest beginnings to become established as a freelance writer. I’m not bragging, but I’ve literally become more successful at this than I ever dreamed was possible. Quitting my job in 2010 to be a full-time freelance writer was absolutely one of the best decisions I’ve ever made in my life! I’ve been home with my kids almost every day as they grew up, I’ve spent lots and lots of time with family and friends, I’ve traveled to New York and L.A. and San Francisco and Europe, we’ve taken marvelous vacations, and I almost never set an alarm clock. It’s a sweet, beautiful life.

And yet…now it’s 2017, and I decided to hire a business coach. Not because things aren’t going well, but because I wanted to see if I can re-evaluate a few things and realign a few goals and otherwise give my career a tuneup to make things EVEN BETTER.

Pamela Slim – My business coach!

And I decided that I wanted my business coach to be Pamela Slim. I’ve hired writing-specific mentors and coaches in the past, and it was always worth the money, but I had some particular goals and interests that I wanted to talk about with Pam this time. I’ve been feeling kind of down in a rut lately, feeling kind of directionless; I needed to rediscover my zest for work. I also recently had a few big projects fall through, and I realized that my pipeline of new projects was looking kind of empty – I hadn’t been doing any marketing in awhile to find new clients, because I’d gotten comfortable (and maybe a bit complacent) from lots of repeat business and referrals and random lucrative projects that landed in my lap. So I needed to think differently about how to find some new freelance writing clients.

Pam Slim has a great sense of optimism and abundance about her, she’s great at building community, and she’s a successful book author and public speaker and corporate trainer and business coach, all of which are things that I would potentially like to do.

So I signed up for individual coaching with Pamela Slim, and also signed up for a 6-week group class with Pam’s network of people called Giant Client Magnet – where we each commit to taking action on 3 or more Tiny Marketing Actions (TMAs) each day to move our businesses forward.

Let me say: BOTH of these business coaching programs have ALREADY been WELL WORTH THE MONEY.

Here is why hiring a business coach is (almost always) a good investment for your small business:


Even if I don’t get any new clients from working with a business coach, even if I don’t get any “new” ideas on what to do for my career by working with a business coach, working with a business coach is already a good investment because it’s helping me hold myself accountable.

Working with a business coach helps get you to actually DO THE THINGS that you ALREADY KNOW you should do.

Maybe this sounds incredibly simple, even stupid! But listen: sometimes when you’re self-employed, the hardest thing to do is to just DO THE THINGS that you already KNOW you should be doing!

For example: I had a whole To Do list that was like 15 items long that I already knew I needed to do – and knew how to do – in order to market my business and find new projects. Many of these things were very simple and easy, like “Send an email to a current client and ask for more work.” But I wasn’t doing the things!

But now that I’m PAYING MONEY to a business coach? I have skin in the game! I have a vested interest in actually getting done with stuff! And I have a new sense of inspiration, because…

New Perspectives

Your business coach will help you see the bigger picture of where you want your business and your career to go. A good business coach helps you think strategically and identify your own points of mental resistance – what are you struggling with, and why? How can you remove obstacles that are in your way? How can you drill down to the roots of what you really love about your business and what you really do best and what you really hope to achieve in the world? With my business coach, I am thinking more EXPANSIVELY about my career and my future and what kind of an impact I really want to make in life.

Business coaching isn’t just about technical/practical knowledge like “which email marketing software to use” (although there’s nothing wrong with that); business coaching, at its best, is CAREER THERAPY.

And that’s what I needed, was Career Therapy. Because sometimes even when you’re successful, you can still get into a rut; you can still get complacent, you can still start to get into a funk and feel like work and life aren’t as meaningful as they used to be; you can still feel human vulnerabilities and anxieties about the future.

The best thing about being a solopreneur is that your success is all up to you – there’s no corporate bureaucracy holding you back, there’s no ceiling on your success!

The worst thing about being solopreneur is that your success is all up to you – there’s no clear path of “next steps” and no higher-ranking people to mentor you and tell you that you’re doing a good job and that you’ll be rewarded someday with a comfortable career path.

Sometimes it feels lonely to be a solopreneur. Sometimes you need a supportive voice from someone more experienced who can help you find clarity and purpose and a more hopeful path forward.

A good business coach will help you put your worries and indecisions to rest and redirect your focus to the present, and give you…

New Energy

Before I started getting business coaching, I was feeling stuck. I knew what I had to do to get new writing projects and get work done and make more money, but I wasn’t doing them. My list of To Dos was just sitting there, clogging up the system like a fatberg. (Do you know what a fatberg is? It’s an amazing new word that I just learned today – a fatberg is a large concrete-like mass of sewage mixed with fats and grease and garbage that clogs up sewer pipes. London has a massive fatberg right now that weighs 130 tons and is going to require a team of sewer workers to work around the clock with hand tools and power hoses to get it dislodged! Fun stuff! Whatever they’re paying those sewer workers, it’s not enough.)

But that’s what happens to your mind when you procrastinate for too long: you get a fatberg in your brain! Your mind gets clogged with a big blob of greasy, messy filth and you can’t move forward, and the longer you ruminate on it, the worse it gets! The filth just keeps building up and solidifying and getting bigger and scarier and messier and nothing can break through!

But now my fatberg is gone! I’m thinking clear and flowing freely! I’m open-minded and energized! I’m ready to see where this leads!

Actual photo of me after dislodging the Mental Fatberg

Here are a few of the things I’ve discovered about what I want to do next with my work as a result of working with my business coach:

  • Building Relationships With Writing: I love to write, I love the craft of writing, but what I really love on a more fundamental level is Building Relationships With Writing. It’s what I’ve spent my whole life doing, ever since I was a 6th grader writing the Gran Family Newsletter (new issues published monthly, printed with a dot matrix printer, and mailed to relatives all over America). Building relationships with writing is how I met my wife via online dating back in December 2003, and it’s how I’ve built lifelong friendships and a following of “fans” on Facebook. And of course, I love to build relationships with my clients and help MY CLIENTS build relationships with their key audiences with the power of the written word.
  • Teaching: I have teaching in my blood. Both of my parents have worked in education, all four of my grandparents were teachers and superintendents and college professors, and my first job out of college was teaching English on the JET Program in Japan. I want to try to do more with this – whether it’s working as a business coach to new freelance writers, or whether it’s incorporating teaching into my career by offering webinars, or whether it’s using a “teaching” approach to inform the content I create for my own website and for my clients.
  • Public speaking: In addition to writing, I love to speak to audiences. I do standup comedy, and I have a following on Facebook – I used to do comedy gigs around Iowa and the Midwest, and hundreds of people have paid money to come to my shows in Des Moines. I want to do more with public speaking, whether it’s as a guest speaker for local associations and networking groups, or speak at conferences, or maybe someday become a keynote speaker and author. I feel like I’m a better speaker than most writers, and I’m a better writer than most speakers. Surely I can do more with this.
  • Helping people find meaning: Ultimately, I’m trying to make the world a more meaningful place. One of the things that makes me good at what I do as a freelance writer is that I have a strong sense of curiosity and a strong service orientation – I can find something interesting about almost any subject. I can find something worth saying about almost any client’s business – and not in a superficial or sycophantic way; I really try to go deeper into what makes that client’s business meaningful and why that business matters. People make meaning of the world through telling stories, and I have been doing that all my life. Ultimately, meaning is what we’re craving. The world is full of bland corporate chain restaurants and cheap mass-produced junk and impersonal clutter and disingenuous marketing messages and lots of other stuff we don’t care about, stuff that’s meaningless to us – but what people DO care about, what people CRAVE, is finding messages that resonate with them, finding people who they “click” with, finding organizations with integrity and values and transparency. This is the great promise of the Internet that we have barely begun to explore: the Internet as an engine of genuine human interconnectedness and a vehicle for human meaning.

I really believe that the next wave of the Internet is not going to be about clickbait or copycat traffic-scraping content from too many sites chasing the same SEO keywords – it’s going to be about creating meaning and genuine connection with people through radical transparency – authenticity, humility, honesty. Just like people are making deep friendships on Facebook with people they’ve never met in real life, the Internet is still a wide open canvas for building relationships – if you’re brave enough to let your humanity through.

That’s been one of the great revelations of the work I’ve been doing with my business coach – I feel like something is opening up inside of me; I feel a great clarity of purpose, I feel completely unstuck. No more fatbergs!

I’m not sure how long these good feelings are going to last, but I hope it’s a long, long time.

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