203: How to Stop Just Listening to The Side Hustle Show and Start Taking Action

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Today’s contribution comes from Heather Gray, a clinically trained Executive Coach and Corporate Therapist with 15 years of experience.

She reached out to me with the post-title pitch and I thought it was a compelling angle, especially now that we’re 200 episodes deep into the show. Heather writes at ChoosetoHaveitAll.com, where she busts the myth that professional success and personal fulfillment are mutually exclusive.

She works with clients locally in Wakefield, MA and offers distance sessions through phone or Skype.

Because this essay speaks specifically to listeners of The Side Hustle Show, I’ve also recorded it as a podcast episode.

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Take it away, Heather!


Nothing gives me a shot of inspiration more than when I look at my podcast feed and see episodes like “Zero to 20K a Month” or “Building a Multi-Million Dollar Ecommerce Brand on the Side.”

Those are some incredibly sexy and enticing titles, aren’t they? Then, you dive deep and you listen in.

You hear Jon Haws say, “Once a book is out there, you’re always making money,” and think to yourself, “Damn, Why aren’t I doing that? Why him and not me?”

Yes, why aren’t you doing that?

Because you’re getting in your own way.

You’re telling yourself that those people just got lucky. They had more time, money, support, skills, or knowledge than you. They are somehow the exception to the rule. You convince yourself you couldn’t possibly mimic that kind of success so you go on listening and never start doing.

The only difference between you and these guests is that they took action.

What is the completely uncensored dream you have for yourself?

You might not be interested in podcasting, app development, or writing Kindle Books and you’ll tell yourself that’s why you can’t have a successful side hustle. Those things don’t interest you so there is no opportunity for you.

Well what do you want? What do you dream about building into a business or side income stream? So frequently when I ask this question, I get a blank stare. It’s hard to get really clear on your vision and goals if you keep stopping at the perceived obstacles.

The first step for being successful is to have a clear goal

  • What is the uncensored view of what you want if you ignore the necessary time, funding, experience or knowledge?
  • If you didn’t have to worry whether or not the idea was valid, what would you be doing?
  • What lights you up, gets you excited, and makes you feel curious and inspired?
  • Once you get clear on that, you can start breaking it down by problem solving the obstacles, rather than stopping at them.
  • Without a clear goal, you’ll never start.

Nick’s Notes: I don’t know if I agree with that 100%. I didn’t have a SMART goal in mind or some super clear vision of what I wanted Side Hustle Nation to become when I started, but it was almost something I HAD to do. That’s kind of weird to try and explain, but that’s how most of my projects have started; something I thought would be fun, exciting, and challenging, and hopefully profitable.

Remember, the Journey is the Destination because even if you do have a clear goal in mind, what happens when you reach it? The answer is always the same: now what?

Still, I believe Heather’s goal setting and clarifying questions are a worthwhile exercise. They’ll get you thinking and if nothing else, will certainly help the process of elimination in identifying which tasks won’t get you closer to your goals.

Accept that the hater in your head comes with the territory

We tell ourselves all kinds of stories sometimes. Many start to believe that successes, like the guests on The Side Hustle Show share, don’t come until you believe in yourself, until all of your ducks are in a row, until… Well, you get the point.

Risk and vulnerability come with the package of being an entrepreneur and until you are willing to accept that and take action anyway, you are trapped in your car listening to other people find success.

Fear is not a reason not to do something. Be afraid but do it anyway.

Nick’s Notes: I did an entire show about my side hustle fears (and included the fears of several brave volunteers from the community). Even Jon Acuff, who has “punch fear in the face” as the subtitle of one of his books, admitted that fear never really goes away.

Remember there’s no such thing as the perfect side hustle or perfect timing. There’s just what you can do in the 24 hours in your day. 

Stop learning and start doing

You really don’t need to know all the things. Not yet. Not at the beginning.

Of course you’d feel more confident and ready if you had the website, systems, and strategies all nailed down before you began–but that’s a trap.

It provides a sense of psychological safety against the risks, doubts, and vulnerability that come with entrepreneurship, but all that learning can keep you standing still.

You don’t need to listen to all of the podcasts, watch all of the webinars, and take all of the courses before you start.

You just need to know what’s next, learn that, and do that. Say yes to the idea or the opportunity and then figure it out. Don’t wait until all of the pieces are in front of you.

Nick’s Notes: I first heard the term “just in time learning” from Jeremy Blanchard on a very early episode of The Side Hustle Show. And while I don’t always succeed in practicing it, it’s stuck with me and I think is a noble aspiration. 

There are tons of things to learn, but far fewer things I need to learn to accomplish my next action item. In a way, just in time learning helps reduce distractions and keep me on task. 

Just start

If you’re anything like me before I started building my online business, you signed up for all kinds of lists and freebies. You have more checklists, PDFs, and tip sheets than you know what to do with. Only focus on the beginner tasks for those just starting out and get to work actually using them.

  • Write down every idea you’ve had since you first started daydreaming about passive income and having a side hustle. Which one makes you the most excited? Which one do you see yourself doing? You have to start somewhere. Picking what’s next doesn’t mean picking what’s forever.

Nick’s Notes: Remember, the best opportunities aren’t visible until you’re already in motion. For me, “just start” is frustrating advice when you don’t know WHAT to start, but the truth is it really doesn’t matter. Yes, I’m just as fearful–probably moreso–of making the “wrong” choice and picking something that will flop, but even that practice helps me get better and spark new ideas.

If you’ve been listening to The Side Hustle Show for any length of time, you’re already armed with dozens of viable business ideas; everything from blogging to ecommerce, freelancing to software. And if you’re still stuck, there’s a laundry list of ideas at SideHustleNation.com/ideas.

  • Name your business and get that URL. Sure, you may pivot away from your original idea or dream later, but when you give your dream a name, it becomes real. It puts a stamp on the idea that you are doing this. That it’s happening. It’s easier to move when you make it real.
  • Find no more than 3 how-to resources for your big idea. Truthfully, three is actually too many but information will give you confidence. These could be tutorial blog posts, books, podcasts, or courses.

Nick’s Notes: That means from each Side Hustle Show episode you listen to, take a minute at the end to write down ONE thing you’re going to implement in your business. And then before you consume any more content, go do that thing.

  • Dump anything that you have collected that is irrelevant. Unsubscribe and unfollow anyone you are no longer interested in. Only accept content from mentors and people you have come to respect and whose vibe you’re attracted to. An avalanche of info in your inbox is overwhelming and will halt your progress.

Nick’s Notes: I hope I make the cut, but if I don’t, that’s OK. I’d rather have you take a week or a month or a year heads down hustling and seeing results, and then come on back when you’re ready for more. I’ll still be here!

  • Schedule time to work on your business and make it non-negotiable, as non-negotiable as a meeting with an actual person. Put it in your calendar. Keep that time sacred. If you have to reschedule it, commit to finding another time. Don’t just wait until next week.

Nick’s Notes: Time blocking has been really helpful for me. I live and die by my Google Calendar.

  • Learn an organization system. I like SCRUM but I also use content calendars and good, old-fashioned pen and paper. You have to map out your attack plan for your dream into steps. Find the system you buy into and choose that. Easier is always better.

Nick’s Notes: It’s just pen and paper for me. That, and time-blocking on the calendar. For longer projects I’ll create a dedicated project workbook and timeline in Excel. Remember though, Step 10 doesn’t matter if you never act on Step 1. 

  • Find a coach, accountability partner, mentor, or interest group. When you’re just dreaming in your head, it’s easy to put your dreams off until later. Find someone who is a couple of years ahead of where you want to be on your journey and partner up. I initially hired a coach because I had no clue what I wanted to do. She helped me develop a vision and then I joined a coaching group to work on implementation and execution.

Nick’s Notes: A mastermind group can be helpful for this and there are Facebook groups related to just about every side hustle imaginable. Just search. 

  • Invest in yourself. This one is always controversial because people like to be scrappy and do it all themselves. However, I went into debt for my dream and don’t regret it. Both my coach and my website designer were put on a credit card. That’s not everyone’s thing, I know, but I knew tech would always be my weakness and I knew that without a clear vision, I’d fail before I began so I set myself up for success by sticking to what I did best and hiring the hard parts out.

Nick’s Notes: This advice makes me a little nervous because I don’t like to see anyone going into debt, but I’ll agree with the sentiment. Sometimes businesses have startup costs. You can be still be scrappy and bootstrap but sometimes you have a spend money to make money. The example I’ll give is when I finally broke down and paid for LeadPages. My business is almost 40x bigger now, in part because I had a tool that made it easier to grow.

A few weeks ago, Rosemarie Groner gave the example of investing in the Elite Blog Academy course and following it step-by-step, with amazing results. 

Swallow the mindset medicine

Paulo Coelho reminds us “the only thing that makes a dream impossible is the fear of failure.”

Jack Canfield tells us “everything we want is on the other side of fear.”

Michael Hyatt challenges us not to fear failure, saying instead we should fear being in the same exact spot next year as we are today.

We all know this. We see these quotes and we pin them, share them, and post them. They don’t work, though, until you start living themuntil you move.

Inspiration and motivation mean nothing without action.

You have to move. It’s non-negotiable. Get clear on what it is you want, wave to the hater in your head as you pass by, and take action.

The ONE Thing Question

What is one thing you could do today that gets you closer to being the person you want to be and the life you want to have?

What’s the ONE Thing I can do right now such that by doing it everything else will be easier or unnecessary?

Start every day with that question and put the answer into action. Maybe then, you’ll be the next one getting the call from Nick Loper, asking you to be on his show.

Start hustling, Side Hustle Nation. You’ve got this.


Heather Gray is the owner of Choose to Have it All.com.

She is a clinically trained Executive Coach and Corporate Therapist with 15 years of experience. Heather works with her clients to identify what they want but don’t have and teaches the movement required to get it. Follow her blog and find her on Facebook.

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

5 thoughts on “203: How to Stop Just Listening to The Side Hustle Show and Start Taking Action”

  1. Dude. I SO needed this episode. Been spending waaaay to much time learning about smart things to do, and not enough time actually doing those things. Especially love the “implement one takeaway before absorbing more ideas” mindset.

    This may mean you have one less listener for the next few weeks/months, but hopefully I’ll come back with some real results to show off!

    Thanks for the nudge!

  2. This is exactly my problem too. I learn and research until I am too overwhelmed and confused to start! Paralysis of Analysis! I will make a simple plan to just start with one thing and DO IT. TODAY. That is my promise to myself right now. I will be successful! Thank you so much for such targeted articles. Are you psychic or something, LoL!


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