5 Questions to Ask Yourself if You Feel Like Giving Up

We’ve all been there. That moment when the excitement has worn off, the challenge feels too heavy, and the thought of walking away seems so much easier than pressing on.

I’ll be honest — persistence hasn’t always come naturally to me. Whether it was working on a car that felt like it was beyond saving, recording the first (very awkward) episode of The Solo Coach Podcast, or standing up for my first coaching-themed speech at Toastmasters, my instinct was often to quit before I’d even really begun.

But what I’ve learned — through experience, coaching, and a lot of trial and error — is that persistence is a muscle. The more you train it, the stronger it gets. And when you’re standing at that crossroad, wondering if you should quit or keep going, asking yourself the right questions can be the difference between regret and resilience.

Here and in episode 30 of The Solo Coach Podcast are five powerful questions to ask yourself the next time you feel like giving up.

1. What do I stand to gain by giving up?

It might feel strange to start here, but acknowledging the benefits of stopping can actually help you see the situation more clearly.

Would giving up free up time, reduce stress, or provide financial stability? Sometimes, choosing to stop is the right decision — but we can only know that, if we’re honest about what it gives us.

When I’ve walked away from projects (or been tempted to), I’ve noticed the immediate relief it can bring. But over time, that relief often gets replaced by a nagging “what if?” That’s when I realise the difference between letting go of what no longer serves me and quitting too soon.

2. What could I gain by persisting, even just a little longer?

Persistence doesn’t mean pushing forever — sometimes it’s just choosing to stay in the game a little longer.

When I first launched The Solo Coach Podcast, it was rough around the edges. No jingle, clunky delivery, me reading off notes. But by sticking with it, episode by episode, I’ve seen growth — in my confidence, my delivery, and the quality of conversations I get to share.

Ask yourself: if I gave this another week, another month, another attempt, what could I learn or achieve?

3. Do I really need to quit, or do I just need a break?

Burnout can make us believe that quitting is the only option. In reality, we might just need to step back, breathe, and rest.

As a coach — and as someone who has a habit of overworking — I’ve learned that decisions made in a state of exhaustion or frustration are rarely the right ones. When I’ve paused (rather than quit), I’ve often found new energy and perspective to carry on.

Sometimes what we need isn’t an ending, but a pause & reset. Just like our phones, our own batteries need recharging sometimes, too!

4. Who could help me right now?

We’re not meant to figure everything out alone. Whether it’s a friend, a colleague, a partner, or a coach, speaking your struggle out loud can create new insight.

In my coaching practice, I often see clients arrive feeling cornered between two impossible choices. But through conversation, a third option almost always emerges — one they couldn’t see on their own.

When I joined Toastmasters, I discovered the power of supportive feedback and a room full of people rooting for you. It reminded me that persistence doesn’t always have to come from within — sometimes it comes from leaning on the right people.

And I would add that asking for help isn’t a sign of weakness, it’s a massive strength. All of the greatest human achievements were made possible by a group of people working together as a team. Knowing when to reach out for help is a tremendous strength, versus trying to do it all on your own.

5. If I saw this through, how would I feel at the finish line?

Imagine yourself on the other side. The project complete, the mountain climbed, the mission accomplished. How would it feel? Would all the pain and suffering feel worth it for the rewards? Would the short-term pain feel tolerable for the long-term gain? Would the end justify the means?

I experienced this recently when I delivered my first coaching-themed speech at Toastmasters. I was nervous, I felt underprepared, and part of me wanted to back out, never to return. But on the other side of that speech, I was buzzing — not just because it went well, but because I’d persisted through the discomfort. That feeling made every moment of doubt worth it.

How would you feel, having reached the peak of your mountain? And finally, to conclude…

Final Thoughts

There’s no shame in changing paths. Sometimes, quitting is the wisest move we can make. But too often, we give up just before the breakthrough.

If you’re standing at that crossroads, ask yourself these five questions. Be honest with yourself, lean on others, and remember — persistence isn’t about perfection. It’s about progress, one step at a time.

And if you’d like a thinking partner to help you untangle your options, find clarity, and explore that third path you might not yet see, I’d love to hear from you.

Because sometimes, all it takes to keep going is the right question asked at the right time.

To your ongoing and future success,

- David
The Solo Coach