127: Side Hustle Coaching: When to Pause

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How do you know when it’s time to step back, take a “time out,” or stop the hustle?

There’s no spreadsheet or matrix or formula to give you the answer, but I think you know it in your gut.

And even then, there’s probably a part of me that wants to say, no, this is just “the dip” — keep pushing.

If you’ve been following along with my public coaching series, you know that Wellington has been working some insane hours at his day job. He’s carrying enormous pressure on his shoulders, routinely putting in 60-70 weeks.

Beyond just limiting the time he has available to work on his side business, the stress of it all has been negatively impacting his job performance, his health, and his relationships. I think we’ve all felt similar situations where we just feel trapped. 

Where we left off, we’d just recorded an emotional and vulnerable call with the help of Dane Maxwell from The Foundation. It wasn’t the conversation I anticipated when I set it up, but the feedback on the episode was powerful.

After I recorded the conversation with John Logar (from yesterday’s episode) on pre-selling software, I immediately sent the raw audio file over to Wellington. I figured the story and the tactics would be motivational and get him pumped up.

The response I received was not what I expected:

“I’m going to be very candid about this with you. My life in general has been in a downward spiral for some time and I’m not sure how to pull out of it. To that end I need to either fully or temporarily drop out of side hustle coaching.”

And he went on to share some of the very personal ways things have been going lately, all stemming from a demanding and toxic relationship with work.

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In this episode, which is just 14 minutes, I put forth the idea that it’s OK to hit pause. That we all have seasons in our life and it’s not always “hustle time.”

(And that’s not the same quitting.)

The timing will never be perfect, but there are definitely better times than others. Sometimes to have to take stock of your situation and priorities and cut out what doesn’t fit, or what doesn’t align at the moment.

In this case, recovering health is the first order of business. I let Wellington know that I support him and care about his well-being and his success. And that Side Hustle Nation does too.

And I understand this is a paradox where the sensation of being trapped comes from. You can’t stop the hamster wheel from spinning because you depend on it; but at the same time you need to or you’ll never get off it.

I don’t know that I have the answers; this was difficult to record.

How do you decide when it’s time to take a breather? How do you balance health and hustle? How do you take time to pause when pausing seems impossible?

If you have any insight from your own business, or words of encouragement for Wellington, please be sure to leave a comment below.

12 thoughts on “127: Side Hustle Coaching: When to Pause”

  1. I totally understand what Wellington’s going through–my working life has regularly had doors shut on it so that I’ve had to take a step or two back from pursuing my goals. Wellington, from what I’ve heard from you in the podcast, you’ll be back. You’re a fighter, but right now you’re on your back. And when you’re down there, the only way you can go is up. Best of luck.

  2. An adventure by its very definition is uncomfortable and unsure. If your find yourself comfortable and confident, you’re running chores, not changing anything. The entrepreneur’s life is a roller coaster for that reason. We dare to risk in search of bigger goal or dream while most people are reluctant to try a new brand of coffee. I heard your podcast with Dane a few weeks before I went through a dark place myself. This post hits me right where I’m at so I’m going to share what I kept telling myself this past week.
    1. The highs and the lows don’t last. It will all pass, it’s just harder to remember that when you’re low.
    2. It doesn’t make you weak; it makes you human. Think of the strongest person you know. There are times they too need rest.
    3. Surround yourself with ‘your people’. Your mentors and like minded associates. Friends won’t understand the struggle – your people will. Both your friends and your people will let you cry on their shoulder and offer advice and maybe a stiff drink, but friends usually stop at comforting. Your people will pull you back to your feet and tell you break time is over. They make you remember that your goals and your dreams are still out there, still achievable and, more importantly, that you still want them. Rest, then get back in the fight.
    I don’t usually post comments, but this seemed like a good time to chime in and let Wellington know he’s not alone. Far from it actually – he’s an inspiration.

  3. A really good book to read that focuses exactly on the theme in this episode of Side Hustle Nation is:
    Necessary Endings by Dr. Henry Cloud.

    Awesome awesome book. Highly recommended.

  4. You’re really not alone Wellington, I can very well relate to your situation right now.

    You just have to keep pushing it. I agree with the idea of pursing and taking a break, it’ll give you back your strength and a fresh sense of purpose.

    So I will tell you to just rest a bit and then, keep on striking.

  5. When you can’t push forward, the only thing you can do is hang on. Hang on, preserve your strength, and make yourself ready for the time when the next opportunity comes along. And it always, always will.

    Good luck, Wellington.

  6. Poor Wellington. I think we all agree with his decision to stop pushing and pursuing, to just survive for a while. We’ve all been there. As to your question, Nick, about knowing when to pause: I think joy has to be the barometer. If the joy has gone, if you hate your life and have lost even the excitement that you had for an idea, it’s time to rest and regroup. The idea will be there when you get back.

  7. I missed the episode you referenced in this one. So, I’d like to go back and listen to it before I say anything in too much detail.

    I will say that, like others on here, I definitely feel for Wellington. I think, as you mentioned, it’s a place a lot of us can probably empathize with.

    As far as your question, I wanted to suggest something along the lines of what Karen said. I do think, as you suggested, there is a gut feeling. I think it’s good to listen to that feeling. I also think you should regularly ask yourself this question: when’s the last time you enjoyed doing [insert job, task, etc.]? There are few routines in life we need that aren’t fun (I can think of flossing or brushing teeth). Anything beyond basic health and hygiene should be fun — not 100% of the time — but a good deal of time.

    I’ve had to ask this question of myself and when I have trouble answering that question, I know it’s time to take a step back and take that breather. I agree it doesn’t mean things are done or that you’re quitting. But, that breathing room is really important. You may never go back to it or you may only take a few days to recenter, but either way, you’ll find something that brings you happiness.

    Good luck, Wellington. You can find happiness and you deserve to find it. I’m sending happy thoughts your way. Keep on striving.

  8. I’ve been there Wellington! I applaud you for being brave enough to do coaching on-air with SHN and allowing such vulnerable thoughts to be shared.

    I agree there are highs and lows, but mostly a season for everything. enjoy your break. Don’t let doubt rob you of that either. Reconnect with family. Show them you care about them and that you’re a team. When you’re ready to resume, you’ll know. Live in the moment and cherish the things you do like about your 9-5. There has to be something, dig deep to find it and focus on those blessings. Take care man! We’re rooting for you.

  9. My heart went out to Wellington in this episode! Hoping he is taking some rest and relaxation time. It’s so hard to get stuff done when we’re exhausted- I’ve been there and I can relate.
    I have no doubt Wellington will come back, refreshed and re-energized, ready to evaluate what he’s done and his pivot strategy.
    Wellington opened up himself to us in a very vulnerable way. I appreciate his authenticity.

  10. I 100% understand where Wellington was coming from and that is why I ended up quitting my job last year and basically running away to Australia. I had nothing left to give. The tank was on empty and I was basically having a nervous breakdown. I only had myself to manage-not a family and I wanted: better friendships, to date, to have a family and working the way I was wasn’t going to facilitate that reality. I had to take a break in order to figure out a better way to get towards where I wanted to go. I think this is probably the most important podcast you’ve done because it brings up the importance of listening to yourself. I wish Wellington the best!

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