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10 Must-Ask Questions Before You Quit Your Biz


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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. 

Focus on fulfillment, go beyond the trappings of success.

Over our time working together, Jenny and I dove into many of the following thoughts and questions. Today, I invie 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.

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).

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