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3 Questions to Ask Before You Quit Your Job

3 Questions to Ask Before You Quit Your Job

Just over a year ago, I quit my job to try my hand at being an entrepreneur—before I knew what that really meant. What I wanted to do was create something that matters, do work that is meaningful in some way.

This isn’t one of those success stories about quitting the corporate world to instant happiness and wealth. Far from it.

My path was up and down, up and down.

  • I got great clients, and then hit roadblocks when I lacked clear communication.
  • I hired a staff, and then downsized 100%.
  • I hated dealing with finances but then took on all accounting tasks myself.
  • I loathed standing in long lines at government offices but then learned how to do all of that online.

Hindsight is 20/20, and there are some things I just wish I had known before quitting my job. 

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Here are the three questions I wish I had asked myself before quitting my job, if only to make the transition smoother:

1. Is the market ready for my idea?

The first fear I faced when contemplating a job move was this:
What if I don’t make any money?

Leaving a job’s security is scary, but very worthwhile if done right. If you truly want to go out on your own, consider the market carefully and consistently. Chances are you have great skills you can offer clients, but you may also want to develop some kind of product offering (like an eBook), too.

Here are some questions to ask yourself about whether or not the market is ready for you:

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  • Is there a need for my service or product?
  • How much are my competitors charging for similar offerings?
  • Can I do what I want to (write eBooks or become a painter) while maintaining the lifestyle I dream of?
  • Who are my potential customers: big businesses, small businesses, individuals, athletes, moms? (The more specific you get, the better your results will be.)

Being clear on how well your ideas and plan fit into the market will help you avoid so many headaches in the future.

2. Is my idea ready for the market?

Brainstorming a new project or idea can be so much fun. It’s the creative process that feels freeing and light—it’s a direct manifestation of the purpose that drives us.

To make any idea work, however, there are some things that go past brainstorming. For example:

  • How will you price your product to achieve your goals?
  • How will you reach your potential customers?
  • Will you make money off your idea forever or just one-off sales?
  • If your customers have questions, how will you handle servicing them?
  • How will you manage expectations when you gain a new customer or project?

These are just a few issues I struggled with starting out. There are many more questions to answer in preparing your idea for the market.

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The only real way is to read, read, read and study, study, study what is out there.

3. Who can help launch my new project?

This is probably the question I missed the most in the beginning of my quest to living an awesome life out on my own. I can’t even imagine all the mistakes I could have skipped and all the connections I could have made if I had given this question the thought it deserves.
A community of peers gives an idea superpowers, launching it to success.

Once I discovered this amazing superpower, it became the most used tool in my toolset.

When I have an idea or a doubt in my mind, I turn to my small tribe of peers. I probably call on them way too much! Their input, though, is invaluable. Without their final touches, I could never have reached sustainability, freedom, and happiness.

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To enlist the help of awesome people, I reach out online just as much as in person. I’ve made great friends through Twitter, but my favorite way of connecting and collaborating with people is through events like conferences. By combining the physical and digital world, I find relationships truly thrive.

What This Means For You

If you are desiring a change in career or a new way to do meaningful work, I applaud your courage—but I also urge you to plan for the ups and downs to come. 

Like everything in life, there is a learning curve. I hope these three questions keep your learning curve from becoming too steep.

If you have any questions or comments, please share them below.

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Last Updated on March 29, 2021

5 Types of Horrible Bosses and How to Beat Them All

5 Types of Horrible Bosses and How to Beat Them All

When I left university I took a job immediately, I had been lucky as I had spent a year earning almost nothing as an intern so I was offered a role. On my first day I found that I had not been allocated a desk, there was no one to greet me so I was left for some hours ignored. I happened to snipe about this to another employee at the coffee machine two things happened. The first was that the person I had complained to was my new manager’s wife, and the second was, in his own words, ‘that he would come down on me like a ton of bricks if I crossed him…’

What a great start to a job! I had moved to a new city, and had been at work for less than a morning when I had my first run in with the first style of bad manager. I didn’t stay long enough to find out what Mr Agressive would do next. Bad managers are a major issue. Research from Approved Index shows that more than four in ten employees (42%) state that they have previously quit a job because of a bad manager.

The Dream Type Of Manager

My best manager was a total opposite. A man who had been the head of the UK tax system and was working his retirement running a company I was a very junior and green employee for. I made a stupid mistake, one which cost a lot of time and money and I felt I was going to be sacked without doubt.

I was nervous, beating myself up about what I had done, what would happen. At the end of the day I was called to his office, he had made me wait and I had spent that day talking to other employees, trying to understand where I had gone wrong. It had been a simple mistyped line of code which sent a massive print job out totally wrong. I learn how I should have done it and I fretted.

My boss asked me to step into his office, he asked me to sit down. “Do you know what you did?” I babbled, yes, I had been stupid, I had not double-checked or asked for advice when I was doing something I had not really understood. It was totally my fault. He paused. “Will you do that again?” Of course I told him I would not, I would always double check, ask for help and not try to be so clever when I was not!

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“Okay…”

That was it. I paused and asked, should I clear my desk. He smiled. “You have learnt a valuable lesson, I can be sure that you will never make a mistake like that again. Why would I want to get rid of an employee who knows that?”

I stayed with that company for many years, the way I was treated was a real object lesson in good management. Sadly, far too many poor managers exist out there.

The Complete Catalogue of Bad Managers

The Bully

My first boss fitted into the classic bully class. This is so often the ‘old school’ management by power style. I encountered this style again in the retail sector where one manager felt the only way to get the best from staff was to bawl and yell.

However, like so many bullies you will often find that this can be someone who either knows no better or is under stress and they are themselves running scared of the situation they have found themselves in.

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The Invisible Boss

This can either present itself as management from afar (usually the golf course or ‘important meetings) or just a boss who is too busy being important to deal with their staff.

It can feel refreshing as you will often have almost total freedom with your manager taking little or no interest in your activities, however you will soon find that you also lack the support that a good manager will provide. Without direction you may feel you are doing well just to find that you are not delivering against expectations you were not told about and suddenly it is all your fault.

The Micro Manager

The frustration of having a manager who feels the need to be involved in everything you do. The polar opposite to the Invisible Boss you will feel that there is no trust in your work as they will want to meddle in everything you do.

Dealing with the micro-manager can be difficult. Often their management style comes from their own insecurity. You can try confronting them, tell them that you can do your job however in many cases this will not succeed and can in fact make things worse.

The Over Promoted Boss

The Over promoted boss categorises someone who has no idea. They have found themselves in a management position through service, family or some corporate mystery. They are people who are not only highly unqualified to be managers they will generally be unable to do even your job.

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You can find yourself persistently frustrated by the situation you are in, however it can seem impossible to get out without handing over your resignation.

The Credit Stealer

The credit stealer is the boss who will never publically acknowledge the work you do. You will put in the extra hours working on a project and you know that, in the ‘big meeting’ it will be your credit stealing boss who will take all of the credit!

Again it is demoralising, you see all of the credit for your labour being stolen and this can often lead to good employees looking for new careers.

3 Essential Ways to Work (Cope) with Bad Managers

Whatever type of bad boss you have there are certain things that you can do to ensure that you get the recognition and protection you require to not only remain sane but to also build your career.

1. Keep evidence

Whether it is incidents with the bully or examples of projects you have completed with the credit stealer you will always be well served to keep notes and supporting evidence for projects you are working on.

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Buy your own notebook and ensure that you are always making notes, it becomes a habit and a very useful one as you have a constant reminder as well as somewhere to explore ideas.

Importantly, if you do have to go to HR or stand-up for yourself you will have clear records! Also, don’t always trust that corporate servers or emails will always be available or not tampered with. Keep your own content.

2. Hold regular meetings

Ensure that you make time for regular meetings with your boss. This is especially useful for the over-promoted or the invisible boss to allow you to ‘manage upwards’. Take charge where you can to set your objectives and use these meetings to set clear objectives and document the status of your work.

3. Stand your ground, but be ready to jump…

Remember that you don’t have to put up with poor management. If you have issues you should face them with your boss, maybe they do not know that they are coming across in a bad way.

However, be ready to recognise if the situation is not going to change. If that is the case, keep your head down and get working on polishing your CV! If it isn’t working, there will be something better out there for you!

Good luck!

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