A helping hand can be the shortcut from a struggling freelance business to a thriving one

When we just start out in freelancing, it’s easy to get caught in scarcity thinking. Paradoxically, that’s the fastest way to poor decisions and bad outcomes. Here’s a good way to make sure this doesn’t happen.

Photo by Unsplash

Photo by Unsplash

When I first went out on my own, I was scared to spend money. Before quitting practicing law, I had dutifully saved up a war chest, and that money had to last until I built up my freelance writing business.

But fear deforms the lens through which we evaluate things.

In fact, scarcity thinking is well known to rob us of the ability to see straight. That's why a swamped executive has no time to delegate and lighten her load. Lonely people avoid seeing friends. Or someone poor may forgo buying insurance but will buy what seems frivolous, like candy.

So on the one hand, I was calculating all business expenses to the cent (it's 10X cheaper to print copies on your laser printer than to make copies at a store). On the other hand, I'd have coffee with anyone who suggested it, wasting untold numbers of hours that I could have used to write and develop my content instead, spending hundreds of dollars on coffee I didn't even want, and coming away depressed because nothing came from most of these coffee dates.

One of the first things that went by the wayside in my push to reduce expenses was my business coach. Walt was (and is) a brilliant business strategist and tactician, who had traveled the path I was now taking. He, too, went from practicing law to doing something different. He, too, had to start his now-thriving endeavor from scratch.

But in my panic about running out of money and seeing visions of ending up living under a bridge, I couldn't justify the expense of coaching.

So I stopped. And soon afterwards I started flailing. I'd read an article about a new marketing technique that every freelancer should know, and implement that. Then hear a podcast about something different, and implement that, too. My messaging and my website kept changing almost weekly. My focus was nonexistent.

My war chest was melting away.

One night, after overcoming a panic attack brought on by the lack of progress in my business, I went back to my notes from my coaching calls with Walt.

And there it all was. A simple, straight-forward path to making my business work. No gimmicks, no "50 ways to capture thousands of new leads," no random coffee dates.

Had I continued my coaching with Walt - keeping the faith, doing the work - I would have saved myself months of wasted energy, a few panic attacks, and 5 different iterations of my business card.

That's the value of good coaching. It only seems expensive if you don't take into account the alternative. Because in reality, it is so much cheaper to learn from other people's mistakes than to make them yourself.

How to maximize the value of coaching

While coaching can be hugely beneficial, especially when you're starting out as a freelancer or if you're pivoting into a new area of writing, there are several things you should keep in mind to find the right coach for you.

1. Clearly define what problem you're trying to solve. "Getting more clients" is too broad and too universal.

  • If you're too scared to even get clients right now because you have no confidence in your abilities, then a coach who works on your craft with you is the first step.

  • If you're trying to answer the question of what kind of freelance business you want and how to figure out basic marketing, then a coach who specializes in startups may be most useful.

  • If you're determined to find clients on the Internet and you can't get the hang of funnels and sales-page conversions, then find a specialist in that field.

2. Decide on a realistic amount of money you're willing to spend on coaching. There are some coaches who are absolutely worth every penny of their $30,000 annual fee, but if that number makes you break out in hives, you may start resenting the coach if the results are not immediate. And resentment does not make for a good learning environment.

3. Decide whether you want one-to-one coaching or group coaching. There are pros and cons for each of them.

  • One-to-one coaching is more individualized, so you get the benefit of a coach's undivided attention. It is also more private - you don't have to expose the warts of your business to other members of a coaching group. On the minus side, one-to-one coaching is often prohibitively expensive and you don't get to the benefit of the experience of other members. You also don't get to build relationships with people who could turn out to be very valuable to your business down the road.

  • Group coaching is cheaper, includes a broader array of opinions and viewpoints, and allows for a greater number of genuine relationships. On the flipside, you're not always the star of the show and don't get as much hand-holding from your coach (although you get plenty of support from the other members of the group).

4. Do your homework. Stalk potential coaches online and see how their material lands with you. Are they too shouty or too zen?  Are they advocating doing stuff that goes against your ethics, or does their stuff motivate you and you feel energized and optimistic?

5. Once you've settled on a few possible coaches, don't make a final decision until you've had a conversation with each of them to make sure your personalities work together and you're feeling a sense of trust with the person.  

You're about to follow that person's advice - make sure your gut feels like you're getting really good advice.

6. Be a proactive participant in the coaching. Coaching is a collaborative process and it works best when you think about your specific questions and challenges ahead of your scheduled interaction with the coach.

Also be clear about what outcome you're seeking from the session with your coach. Sometimes, you may need grand strategy or a reality check. But sometimes, you need a step-by-step roadmap with your coach reading and editing an email you're about to send. Try to be as clear with yourself about what you need as possible.

And be honest with your coach, too. If something the coach says doesn't sound right to you, say so.


And so with a new year staring you in the face, where do you want to be in your business in 2019? Will you go it alone and tough it out or will you try a slightly easier route with a coach by your side?


In full disclosure, we’re launching a small group coaching program in the new year for freelance medical writers.

Maria Granovsky