The Art of Management—For One or Many—With Productive Flourishing Founder Charlie Gilkey

The Art of Management—For One or Many—With Productive Flourishing Founder Charlie Gilkey

The Nitty Gritty:

  • Why to shift from hiring contractors to hiring employees
  • How to keep your team from becoming overcommitted and overwhelmed
  • How to structure time to enhance creativity

This week, my guest is on the Profit. Power. Pursuit. podcast is Productive Flourishing founder, Charlie Gilkey. Charlie is a best-selling author, speaker, blogger, podcaster and business strategist. His website has been visited by nearly 3 million people and his tools, worksheets and planners have been downloaded more than 1 million times. He’s taught thousands of people how to go from idea to done using simple, but powerful approaches that tap into their strengths and genius.

Charlie and I talk about the art of management—whether for one or for many including the shift from contractors to hiring employees, how to keep your team from becoming overcommitted and how to structure time to enhance creativity.

From Contractors to Hiring Employees

I hire and select for people who are versatile, adaptable and like to do multiple things.

— Charlie Gilkey

Although Charlie still has independent contractors on the Productive Flourishing support team, he built a core team of five employees who are all dedicated to achieving the same goal. They all wear many hats and are multifunctional to allow for changes to, and growth of, the business. He found it is harder to build culture with freelancers or contractors. Everyone on the core team who are employees already understands the goals, processes and culture which is sometimes harder with freelancers or contractors who must figure these things out in addition to doing the job they are getting paid to do. As your business grows what you actually need is people who fit your culture, can show up each day to dedicate their time to your business and be flexible.

Control the Overwhelm

If we have to wear 17 different hats, at least know who is wearing which hat.

— Charlie Gilkey

When you have a small, but versatile team of people who “wear 17 different hats,” it’s important to have very clear job descriptions and roles and responsibilities. People are in different lanes of responsibility and different projects that they own. Charlie’s team also uses Asana to schedule regular routines and projects. When people aren’t keeping up with their routines, it’s a sign that they are overcommitted. By knowing what the routines are, when they need to be done and who is doing them, a lot of the meta thinking is not needed. The answers are in the routines. When your team isn’t clear about how things are going to get done, the uncertainty zaps your team’s productivity and morale. Plus, in the last year the team has gotten a lot better about determining the projects they are going to commit to and saying “no” to others.

Structure Time to Enhance Creativity

A lot of creative people don’t recognize how supportive structure and defaults are.

— Charlie Gilkey

A lot of creative people rebel against the very things they need the most. High-performing creative people inevitably have these really well thought-out structures and containers to do their creative work. Productive Flourishing is to the point that the processes and structure are set, so the team can use their creativity on the work and not use it to figure out what the work should be and how it will get done.

Tune into the entire podcast to learn more from my discussion with Charlie including how businesses and professionals make things harder and how he articulates his intuitive synthesis to his team. You can learn more about Charlie Gilkey and download his free planners for creative people from his website.

And, listen to the Productive Flourishing podcast on Apple Podcasts, Google Play, or wherever you listen to this podcast!

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The Secret to Small Business Longevity with Career Coach Michelle Ward

The Secret to Small Business Longevity with Career Coach Michelle Ward

The Nitty Gritty:

  • How to plan and pivot out of a crappy job
  • How a brand evolves and “grows up” over the life a business
  • Why entrepreneurship allows the flexibility to adjust your business when you face a negative or positive situation out of nowhere

My guest on the Profit. Power. Pursuit podcast this week is Michelle Ward, founder and career coach of When I Grow Up, a firm dedicated to helping creative women get out of their “soul-sucking jobs and discover—and launch!—their authentic, fulfilling businesses.” After 20 years of preparing for and pursuing her dream of being an actress, she suddenly realized it was no longer the life she wanted to lead and decided to get a “real job.” We talk about her own transition to discover her own dream career, how the When I Grow Up brand has evolved and how her business became her relief and release after being diagnosed with cancer.

Plan and pivot out of a soul-sucking job

The devil you know is oftentimes better than the devil you don’t.

– Michelle Ward

Michelle started to get beaten down by the business of show business, and decided that even though she had spent her life up to that point preparing for a career as an actress, it was no longer what she wanted to be when she “grew up.” But, she ultimately didn’t know WHAT she wanted to be and she didn’t want to settle for anything less than something she was passionate about. After a lot of soul searching and help from a career change class, she realized being an entrepreneur really fit everything she wanted for herself.

She became the coach that she couldn’t find. But, as Michelle shares in our interview, it took several years of planning and working a “grown-up” job as an executive assistant so she could pay her bills and get her training before she pivoted to a full-time career coach.

Evolution of the When I Grow Up brand

Overwhelmingly, my people told me that they were attracted to me and stayed around because they clicked with the name.

– Michelle Ward

Since Michelle’s name is so common, it never crossed her mind to use her name as her business name. After some deliberation, she settled on the name When I Grow Up because every time she would share it with others, they would laugh and “get it.”

There have been three different logo/brand shifts as the brand has grown up over the years. Michelle has worked with the same designer since the beginning of her business and during our conversation she shares how the look and feel of her brand has shifted. She’s really happy with where the brand is right now and Michelle believes that the caliber of the clients she attracts is a really big nod to the business name, brand, how she shows up online and how authentic she is.

Each year, Michelle creates an infographic to illustrate her business by the numbers that offers a fascinating look into her revenue streams and business expenses.

Adjust your business when necessary

Whether it’s something negative or positive out of nowhere the same rules can apply.

– Michelle Ward

Everybody responds differently to the trials and tribulations of life when being an entrepreneur, but the promise of entrepreneurship is that you have the ability to adjust your business in a way that works for your life circumstances. Michelle shares how she weathered the storms in her business including two different bouts with “boob cancer” in 2011 and 2015. At the forefront of her approach was honesty and transparency with her clients. Michelle explains how she adjusted her business during her surgery and treatment based on what she still wanted to do that made her feel good, what she thought she could manage and how she could alter the expectations to show up at a certain time and avoid feeling guilty if she wasn’t up to it.

I invite you to tune in to listen to the entire podcast where you will hear all the nitty-gritty details from this long-time entrepreneur and learn about a great opportunity to join Michelle at the Pivot Assembly, a virtual event with amazing career change experts, including yours truly, to learn about how to pivot out of your crappy job into a more traditional job or entrepreneurial work.

Each week you can learn from the experiences of successful entrepreneurs to build your own business. Subscribe to the Profit. Power. Pursuit. podcast on iTunes to get the nitty-gritty details about how these professionals built brands and teams and are living out their dreams as an entrepreneur.

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I Fell Last Night: On Preparing For Success

When the warm up exercise included doing monkey bars, I knew I was in over my head.

Rewind to a few weeks ago: I noticed a post on Instagram about our local bouldering gym having a women-only beginner bouldering class.

I Fell Last Night: On Preparing For Success

It was starting in 2 days and–for some reason–I decided I needed to do it. I had no climbing experience. Not even tree climbing.

Superman might have arms of steel. I have arms of aluminum foil.

The very first class wrecked me. I was sore for 4 days.

The second class was better. But I still couldn’t get to the top of the “boulder.”

During the 3rd class,I made it higher than I ever had before. I was just one foothold away from topping it out…

…but I didn’t have one more foothold.

I held on and on and on, trying to figure out how to I could get the leverage I needed to go just one step higher.

Soon enough, my arms and legs started to shake.

At that moment, I shifted my focus from going up to getting down.

Now, there’s only one way down.


I put energy and brainpower into figuring out how to fail–even though there was a giant pad directly under me.

I already had what I needed to fail. I didn’t need to put energy into it. I could have stayed up there until my muscles gave out looking for a way to get over the top.

But I didn’t. And that’s where things got really dicey.

I’ve gotten pretty used to falling in 3 short weeks.

When I fell this time, my neck snapped back pretty good.

Eventually, I had to call it quits because I knew what was happening to my body… and that I was going to have a rough few days with some muscle spasms in my back.

Once I was up from the fall (it really wasn’t that bad), the instructor pointed out that there was, in fact, one more foothold. I just didn’t see it.

I couldn’t have seen it because I let my energy focus on failing instead of forging ahead.

Why didn’t I see it?

I didn’t scope out the route (or the “problem” as we call it in bouldering-speak) before I started.

Because I assumed I would fail.

I have failed every time I’ve attempted to climb so I didn’t properly prepare.

You can bet I won’t be doing that again. I’ll know my line of attack, I’ll have taken account of all of my resources, and I’ll know some options should I get hung up.

And if I fall again? No worries. Falling isn’t bad–but not anticipating what I need to succeed is.

Now, dear reader, this isn’t just a story about my poor attempts at climbing over a fake boulder.

This is a story about your business–of course.

I want to know if you’re planning to succeed or merely paying success lip service.

I want to know if you have all of your energy and focus on your idea of success or if you’re regularly refocusing on what will happen when you fail.

Planning to succeed doesn’t mean just having a plan or even “doing the work.” It means making decisions and taking actions that prepare your business for meeting your goals.

Are you taking into account everything you’ll need to succeed? Or are you spending more time thinking about what you’ll do when you inevitably fail?

For instance, consider your year-end revenue goal. Maybe it’s $50,000. Maybe it’s $500,000. Maybe it’s $5 million.

Have you considered how many customers you’ll have to enroll to actually hit that number?Have you considered the number of hours it will take to service that many customers? Do you have the right team or schedule to process that customer service? Do you have the right processes in place to fulfill orders?

In other words:

Is the business you have now (systems, tech, team, management, service) the business you need to hit your goal?

It’s tempting to think that you need to hit the goal first to have or even earn “that kind of business.”

But you have to build the business that has the capacity to reach your goal in order to reach your goal in the first place.

That can mean making some uneasy decisions about the kinds of offers you want to sell, the people you want to hire, and they money you want to spend. When you’ve planned to succeed and created the capacity to reach your goals, you’ll feel so much more confident actually going out to make it happen.

And that confidence will translate into action that produces much, much better outcomes.

Finally, I want to say that contingency planning is important too. You should know what you’ll do if things don’t go to plan. But don’t let contingency plans inadvertently influence the action you take. That’s how self-sabotage happens.

You can wait for the right time forever

This is Natasha Vorompiova. She helps teams amplify their impact by creating systems for scale.

You can wait for the right time forever

Natasha has made a lot of changes in her business in the years that I’ve known her. What’s more, she’s helped me make a lot of changes in my own business—training our COO Rosie, changing the way I think about business systems, and constantly demanding (in the nicest way possible) higher and higher levels of work from me.

She’s the kind of person who takes intentional and decisive action when it comes to the growth of her business (and her clients’ businesses too).

We spent a week together in the Flathead Valley of Montana talking about what’s next for her business. And, I have no doubt she’ll succeed at making the pivot she’s working on now.

I’ve watched a lot of people make plans to change their businesses over the years.

Some, like Natasha, succeed—they earn more, grow their teams, stay focused, and stress less.

Most don’t.

The ones who don’t succeed wait for the right time to make a big change. They wait for their bank accounts to have a certain amount of extra padding. They wait for their schedules to thin out enough. They wait for permission from the universe, from social gatekeepers, or the market.
Most of these business owners are still at it.

They’re still plugging away at their businesses the way they’ve always worked. They’re still selling the things they’ve always sold. They’re still working the schedules they’ve always worked.

There’s never a right time to make a big change in your business.

There’s only now.

Right now, it’s scary and uncertain to consider pulling the plug on the offer that’s consistently made you money (but sucks you dry).

It’s scary and uncertain to let go of the team member who’s been with you for years (but hasn’t kept up with the direction of your business).

It’s scary and uncertain to stop doing what you’ve always done (but hasn’t given you the results you want).

You can mitigate risk—but you can’t avoid it.

You can’t avoid taking a leap of faith—if you really want what’s on the other side of the gap.

I’m fond of saying that we don’t set big goals to achieve them, we set them to change our behavior.

Changing what you do is the only way you can change your situation.

If you want a different business model, you have to make a change. That likely means you have to stop offering something, start offering something else, and focus on making the new way work.

If you want a different customer base, you have to make a change. That means you have to stop catering to  some people, start wooing others, and focus on building relationships with the new folks.

If you want a different schedule, you have to make a change. That means you have to cancel appointments, shift responsibilities, mark days off, and focus on making that schedule work.

That probably all seems obvious but so few people actually do it.

They wait and wait and wait.

They grow more and more frustrated that things aren’t going to plan. That their plans must be broken. That they’re just not good enough to make it work.


…they haven’t even started on the new plan. Not really.

Now, it’s time for some deep introspection.

Reader: am I talking about you?
If I am, there is no shame in that.
Now you know.

You know that it’s time to make the change you crave.

It’s time to pull the plug, make the call, send the cancellation.

It’s time to start the new thing. Make it happen. Focus your attention.

Because the only time to make the change you want is now.

Rebecca Tracey did just that a couple of years ago. She realized that she wanted more space in her business. She wanted to be able to pursue rock climbing, backpacking, and spontaneous travel.

But she was stuck in a cycle of launching her core offer 6 times per year.

So she pulled the band-aid off.

It required a leap of faith, a bit of investment in going big, and an iron will to make it work.

And now she can take months away from her business if she wants to.

That’s what we talked about in this episode of Profit. Power. Pursuit.
Click here to listen or read more on making a big change in your business to pursue a more adventurous life.

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Fueling Your Business With Live Events with Tradeshow Bootcamp founder Katie Hunt

Fueling Your Business With Live Events with Tradeshow Bootcamp founder Katie Hunt

The Nitty Gritty:

  • Why live events are where it’s at
  • How the sales and promotion cycle of a live event is different than other sales cycles
  • Why it’s important to add to your team to allow you to focus on the tasks in your wheelhouse

We dig into the nitty-gritty details of live events in this week’s episode of the Profit. Power. Pursuit. podcast with my guest Katie Hunt, founder of Tradeshow Bootcamp, a business dedicated to educating and supporting creative entrepreneurs and small businesses. Katie also hosts the Proof to Product podcast. She takes a lot of pride in the events her team creates, and on that podcast she shares a lot of wisdom about what it takes to create events that offer attendees a great experience for learning and having fun, too!

Live Events are Where It’s At

Introverts of Profit. Power. Pursuit., go to live events. It’s completely worth it.

— Tara Gentile

What was to become the live event known as Paper Camp began in 2011 as a teleconference, and the first in-person Paper Camp Conference happened in 2012 once Katie knew there was a demand for this type of curriculum. Katie wanted to build a strong community where people were not just learning something, but they were connecting with others and building strong relationships. She knew that would be much more impactful at live events. Events are a really powerful tool, and although they aren’t right for everyone’s business model, they are hugely successful in helping Katie build the community that she sought to create.

Organization, Sales and Promotion of a Live Event

There’s a lot more that goes into their decision making {to attend an event} than ‘can I afford this and do I want to go.’

— Katie Hunt

Katie and her team work 6 to 8 months in advance to prepare for their next live event. She suggests if you’re doing a live event for the first time, send a survey to your audience to determine the best time of year for them to attend a live event. In the podcast, Katie walks through the steps her team takes to organize a live event, but keeping it simple and streamlined for her attendees and speakers is always paramount.

Since a live event is a higher-level program and higher expense for attendees, it’s important to start the sales and promotion process early since there is a schedule you have to maintain and people need the time to prepare to be away from their families and businesses. As soon as they close registration on one Paper Camp, they begin sales for the next one; however, there are promotional spikes in a three-month period where most of the sales happen. Through the course of the sales cycle, Katie and her team are nurturing their audience through case studies, alumni stories and more to help potential attendees see how their life would change if they attended the event and give them a taste of what they will learn, who they will be engaged with and to highlight the speakers they will interact with and learn from.

Event Teams

You can grow your team organically and in small batches.

— Katie Hunt

Katie has a small, but mighty team of virtual independent contractors, several who are Boot Camp alumni, that take care of the event details so Katie is free to work on the content and higher-level stuff that’s in her wheelhouse. Hiring people to do the work that needs to get done strengthened the content that is offered at the events.

I hope you listen to the entire episode to hear more about Katie’s team, how she manages cash flow when she has fairly large expenses to cover, why she believes in paying herself consistently and how she has turned some of her live events into online courses.

If you liked what you heard on this episode, I invite you to subscribe to the Profit. Power. Pursuit. podcast on iTunes today! Every week I talk to small business owners who share some of the secrets to their success as they build their businesses.

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Creating Systems for Efficiency & Productivity with Indie Shopography founder Emily Thompson

Creating Systems for Efficiency & Productivity with Indie Shopography founder Emily Thompson

The Nitty Gritty:

  • How purchasing a tanning salon when she was 18 set Emily on a track for entrepreneurship
  • Why extremely detailed process management will help you feel more productive
  • How Emily balances the demands of running two businesses

This week, my guest on the Profit. Power. Pursuit. podcast is Emily Thompson, founder of Indie Shopography and co-host of Being Boss, a podcast for creative entrepreneurs who want to up their game. At Indie Shopography, Emily helps creatives build and run online businesses from the design and development of their business websites to marketing and education products. Emily and I talk about the time she bought a tanning salon at the ripe age of 18, why her extremely detailed process management helps her feel more productive and how she balances running two businesses.

Lessons from owning a tanning salon

I remember thinking this would not be my last relationship with business.

– Emily Thompson

When Emily was 18 she worked at a tanning salon one night a week in exchange for getting to use the tanning beds herself. Even though she had never taken a business course and was young, she could tell the business was in trouble. Then, thanks to a combination of moxie and mettle she made a call to the owner and ended up buying the salon and owned her first business at age 18. During our conversation, Emily shares insights about this opportunity and although it was a relatively short period of time, she credits it with giving her the bug to be a business owner. Today, she is very intentional about building a business that really allows her to do work that works for her.

Detailed {often painstaking} to-do lists for optimum productivity

My trick for myself is breaking down those tasks so minutely that sometimes I can check off 5 things in 5 minutes because I really broke them down that small.

– Emily Thompson

Whether Emily is designing a website or developing a new educational product, her process is very much the same. She outlines her entire process in the podcast and emphasizes the power of her detailed to-do lists that break down tasks into bite-size chunks. Once she has that very detailed plan, she schedules it out by using Asana. Even though her to-do list may seem super overwhelming for every project, she knows that tackling each of those individual tasks—that are small and manageable—she will ultimately get to the end of it. When those to-dos are marked off, the end result is a new product or website has been created.

Secrets to juggling two businesses

I don’t have to wear too many hats. They’re the same hats, just different colors.

– Emily Thompson

In the podcast, Emily shares her experiences and thoughts about how to juggle being the boss for two different businesses. She loves that she doesn’t have to put all of her energy into one thing, and that makes having more than one business appealing to her. The two businesses give her enough structure to not pigeon-hole herself creatively into one creative endeavor. She and her partner at Being Boss put together a very detailed marketing calendar annually so that they have a clear view of what’s happening in all three of their businesses so nothing gets lost.

In the full episode, we talk more about Emily’s passion for Asana, the structure of her team, as well as what’s on the horizon for both of her businesses, plus a book launch next spring! I hope you’ll tune in to receive all her valuable insight.

Learn from today’s most innovative and inspiring entrepreneurs every week by subscribing to the Profit. Power. Pursuit. podcast on iTunes when you want to know how small business owners really manage their time, develop outstanding products, build their teams and get new customers.

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Tara Gentile is on a mission to turn the small business owners of today into the economic powerhouses of tomorrow. She's the creator of Quiet Power Strategy®, a business design system and entrepreneurial family. She's also the host of Profit. Power. Pursuit., which Entrepreneur named one of the 24 top woman-hosted business podcasts.