10 Must-Ask Questions Before You Quit Your Biz

by Alli Polin on September 8, 2015

fork in the road

Whether you have a small business, work inside of a corporation, or are retired and starting round two, chances are you’ve struggled to feel successful at one point or another. Maybe your big ideas and confidence gave way to the reality that it’s harder than you thought or harder than others made it seem (from the outside looking in). Before you quit, ask yourself the questions below. Use it as your checklist to reflect and redesign before you resign.

Before we jump into the questions, with my client’s permission, I wanted to share a part of her journey in the hope that you may see an echo of your own. Jenny wanted to create a business and do work that made her feel fulfilled, whole, like she was living with purpose. Sound familiar?

Once a manager in a large organization and now a stay-at-home mom, she wanted to rejoin the workforce and decided to become a coach. In a flurry of activity, she took a coach training course, built a website with a blog and even got a couple of subscribers with her first few posts. She’d been on Facebook forever and as a part of her business launch created a Twitter profile, LinkedIn profile and, of course, jumped on Instagram and Pinterest too.

She posted and waited. 

She blogged and waited.


It was time to shake things up, and she went to the Chamber of Commerce and attended a networking event quickly followed by two more. One of her new contacts invited her to BNI, so she went there too.

She networked and waited.


Someone told her to email her contacts to let them know about her services, so she did. She wrote a long email offering a sample session over coffee and sent the note to all of her gmail contacts and blasted LinkedIn too.

This time, a few people sent a note of congratulations in return.

Clients? Zip. 

Enough waiting, she took it a step further and donated her services to an auction at her child’s school. She was guaranteed a client even if the money wasn’t going in her pocket.


They did their three sessions and when time was up, they parted ways.

By the time she contacted me to start coaching, she was demoralized. The question she posed was “Should I just give up?” She qualified it with “I’ve done everything I can, and it’s not working.”

There’s a lot packed in that statement, “I’ve done everything…” and I’m still struggling with success, aka a failure. 

Over our time working together, Jenny and I dove into many of the following thoughts and questions. Today, I invite you to reflect on your experience. If the answers don’t roll off of your tongue, sit with the questions, they’ll come in time.

10 Questions to Ask Before You Quit and Give up on Your Biz

1) What’s fulfilling?

What do you absolutely love to do? There are many ways to apply your passion, don’t box yourself in before you break free from your expectations and assumptions.

2) What is success? 

What does success look like to you? Big corporate-like success, something small yet robust or what? Try to move away from a dollar figure your primary answer to this question. Instead of “I want to make $100,000 a year,” try “I want to pay my mortgage, car, buy gifts for people I love and go on vacation.” It may take far less dollars to create the life you want than you think.

3) Are you falling short of what you see others accomplish, yet on track for what you want in your life and business?

Stop comparing. Anyone who tells you that following a path to success that someone else paved will work for you is a liar. You need to lay each brick on the road with your work and effort.

4) What do you offer? How is it the same and different from the 25 billion other people who do what you do?

Be clear on what you offer and how YOU do it. Don’t compete on price, you bring too much to the table to be defined by the $$ in your proposal or your bank account.

5) Do you only share what you know or who you are too?

Be vulnerable, people want to work with another human being, not only a brand. Enough said.

6) When was the last time you truly pushed your limits?

Leave your comfort zone – by miles, not inches. Brainstorm for a minute or two on the things you could do and make yourself uncomfortable (leave judgment at the door). Now, decide what one you actually will do from a “leap” mindset instead of a “fail” mindset. You can always come back to your comfort zone to reflect and regroup, it’s not your enemy.

7) How will people engage with you?

Create a diversity of ways for people to engage and hire you. Is the only option face to face? How else can people tap into your expertise, even on demand? Don’t gloss over this question just because “that’s the way it’s done” in your industry. Get creative.

8) Is every step draining your energy?

Not everything you do for your business is going to be the fun stuff. However, equally true, not everything you do should be so gosh darn awful you hate every moment of it, or it’s 10% fun and 90% pain. Even hard work can be energizing when you’re doing the work you’re meant to do. Look at your ratios and be honest. Changing up what you’re doing may help your energy to soar too.

9) Are you hiding behind “I tried?”

Telling yourself that you’ve tried and failed is an excuse to stop. Dissect and reflect instead. Write down what worked from each of your attempts (even if it mostly was a bust). It’s easy only to see the bad, look more closely to find seeds of success to carry forward.

10) Do I quit and move on or keep going?

If you’ve truly pushed as far as you can, have lost your passion, or found a new one, it may be time to move on. This is a question that you often can’t answer without working through the nine that came before. The only word of caution I can offer is not to let your emotions dictate your decision. Struggle is painful, and we’re wired to get rid of the pain and find ease once again. However, when you give up on something that truly matters, that hurts too.

Don’t believe people who tell you that giving up isn’t an option, it is – so is reinvention. Get clear on WHO you want to be, WHY you’re letting go, WHAT you want to do now and HOW you can make it happen (define your next step even if you don’t know the last).

What questions would you add that you’ve found helpful?

To get clear on your values and vision in addition to defining your step forward this eCourse if for you: Get Unstuck and Choose to Move. No more wondering, debating or nail biting. Get clear now. 

{ 20 comments… read them below or add one }

Carl September 8, 2015 at 10:34 am

Great post Alli, I especially resonated with your side bar “You can do whatever you want….just go for it.” It is that ‘intention-ality’ that will open doors that you didn’t even know existed.
Appreciative of your work,


Alli Polin September 8, 2015 at 6:13 pm

Thanks, Carl. Yes definitely need to travel to where intention and permission meet. So often, it’s permission to go all in (or get out) that’s stopping us short of fulfilling our intention. I’m with you too – amazing what happens when we fully embrace and own it!

Big thanks for sharing your thoughts!




John Bennett September 8, 2015 at 11:44 am

My very strong belief is that everyone needs to push beyond the limits AND everyone must know what their definition of success is!!! So often we don’t have a definition of success, thinking ‘I’ll know it when I see it’ or, even worse, I want to be ‘better that XXX.’ Find your passion, decide what success will be following it, and honestly strive for that success. If the passion or your environment change, time to move on… without kicking yourself or even a chair!


Alli Polin September 8, 2015 at 6:17 pm


I’ll know it when I see it often = doom! (as does simply the desire to outpace the competition) So glad you brought it up. You have to know what you want so you can make all of your choices and decisions to make it happen. Wandering after the latest shiny object will keep you busy but likely not headed where you want to go.

Also, we do need to allow that our passion may shift over time and instead of viewing that as giving up, I think it’s an opportunity to reframe as moving forward to continuing to create a life of passion, purpose and most of all meaning and service.

Grateful for your comment!

~ Alli


Stephen Lahey September 8, 2015 at 1:04 pm

Enjoyed this post, Alli! In my experience, coaches who first develop an accurate understanding of their ideal clients (target market) and know exactly what these folks want will have a lot more clients than those who don’t do that upfront. This is because they have the knowledge to create a targeted, effective value proposition and a sales and marketing strategy that helps them acquire the right clients on a consistent basis. It sounds like your client may not fully understand what their target clients want most and/or how to sell to them. Is that possible?


Alli Polin September 8, 2015 at 6:23 pm

You bring up a central struggle for many life coaches (and yes, I left out the niche question here which is incredibly critical for all business owners – who do you serve?)

Often, life coaches believe they serve “anyone with a life” in essence, everyone. While I agree that they may have the skills to help people everywhere reflect and create meaningful change, it does not mean that every person on the planet is their target audience.

Niche and target market is often the difference between a thriving business and a floundering one, even in the same industry. Thanks for bringing it up here.

Readers: If you are a small business owner, I strongly encourage you to subscribe and listen to Stephen Lahey’s podcast specifically for small business owners. Fantastic resource!



Kate Nasser, The People Skills Coach™ September 8, 2015 at 3:11 pm

Very momentous post Alli. Just think of how many first time entrepreneurs have been down this path. Great contribution to every would be business owner and business owner — as well as contribution to the blog-o-sphere.

I will be sharing this on my streams for sure!


Alli Polin September 8, 2015 at 6:30 pm

Thanks, Kate! It’s a big decision when someone considers giving up their business. Sometimes, with help, they can refocus and move forward with new energy and possibility. Other times, a coach supports them to let go, never a decision that comes lightly. I hope that people will come across this post and be able to get underneath what’s right for them.

Grateful for your support and comment!

~ Alli


Terri Klass September 8, 2015 at 7:45 pm

You really wrote an important post, Alli! Many of us who are solo entrepreneurs can become overwhelmed and feel so isolated when our business runs slow. For me, I find reaching out to people for help, information and ideas can be so energizing. Once I realized that being vulnerable and admitting I really don’t have all the answers, I was able to get the help I needed.

Also, reminding ourselves that we may be good at certain tasks but should either hire others or strategize with others for areas of less expertise.

Thanks for another great article! I am looking forward to sharing!


Kate Nasser, The People Skills Coach™ September 8, 2015 at 8:35 pm

I agree Terri. And what is very interesting is how much easier it is to reach out today on the WEB than 25 years ago w/o the WEB!



Alli Polin September 9, 2015 at 9:02 am

I agree, Kate! So much easier to foster a vibrant network of collaborators and supporters than ever before. Here’s to moving beyond the Chamber 🙂


Alli Polin September 9, 2015 at 8:57 am

Terri –

Thanks for bringing up isolation. I think that many people who move from corporate positions to solo practitioner struggle with isolation at one point or another. It’s one thing to network and another to build supportive, sustaining relationships. It can make all the difference between giving up and pushing forward.

… and a big yes on accepting that we can still build a team around us! We don’t have to be experts in everything!

Great additions! Thanks, Terri!


Jon Mertz September 8, 2015 at 7:51 pm


“I tried.” In many ways, these two words can get someone more stuck than anything else. “I tried” becomes a rationalization, rather than trying something more or something different. “I tried” is passive. “I am trying” is active. We need to stay on the active side.

I am not suggesting spinning our wheels, but I am suggesting we need to not use what we tried as an excuse to not do something else. Anyway, that point resonated!

Thank you!



Kate Nasser, The People Skills Coach™ September 8, 2015 at 8:34 pm

Very interesting thought Jon Mertz. Can be very very true!!


Alli Polin September 9, 2015 at 9:00 am

I tried. I can almost hear the sigh just hearing those two words run through my head. It’s throwing hands up; defeat.

What I appreciate is your consistent ability to help others to activate their leadership. One small shift from past tense to present is a call to action and a commitment to giving it our best before making the choice to move on – not simply give up.

Many thanks, Jon!


Karin Hurt September 9, 2015 at 9:45 am

This a fantastic list. Most small businesses fail, not because they have a bad business model, but because it’s often very discouraging at the beginning. Having launched my business a year and a half ago, I can tell you for sure… it takes time! It’s tempting to think that the seeds you are planting aren’t doing anything. I’ve been pleasantly surprised how seeds I planted over a year ago and blooming now. The trick is… no waiting. Plant. water. repeat.


Alli Polin September 10, 2015 at 2:03 am

Yes, yes and yes! One seed and the wait will take forever… and you never know what will bloom. Excellent advice!


Chris September 9, 2015 at 9:10 pm

I’d add the question WHO ARE YOU DOING THIS FOR?


Alli Polin September 10, 2015 at 2:04 am

Absolutely!! I got great advice early on to create a detailed profile of my “who.” Where they shop, live, hangout etc. Took an abstract group of people and made them real.

Great addition, Chris! Thanks!


Chery Gegelman September 13, 2015 at 1:25 pm

Hi! I’m late to this party. But I LOVE your post!

Such powerful reminders about why we do what we do and how to make sure we are tapped into our purpose and passion.

Thank you and I’m sharing!


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