How to Quit a Job Properly

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How can you quit a job that you hate, or feel so-so about and replace it with a dream job or a business that can grant you the freedom you want and money that you desire? 

Three years ago, I quit my 9-5 job as a marketing assistant at a fortune 500 company to start my own business. Now I’m a 7 figure business owner and I haven’t looked back.

In today’s blog/podcast episode, I came full circle and had the chance to interview my old manager, Tiffany Uman, from my previous corporate job! 

Yes! The same company that I left three years earlier! 

In this article, we’ll cover what you should do if you have a side hustle, how you can balance it with your full time job as well as advice on how to quit your 9-5 properly, without burning any bridges. 

Tiffany Uman is a Fortune 500 Senior Director and a Career Strategy Coach. Her mission is to guide as many young professionals as possible to take control of your career success through her proven, best practices without the struggle, frustration or time lost by figuring it all out on your own!

Quitting your job is hard, and scary but the tips in this blog will help you through it. 

Quitting a job is scary, especially if you’re just starting out in your career or have been in that position for a while. When you’re about to quit, you have all these thoughts and what is running through your head. Will people be disappointed in me? Will my managers be upset with me? But I’m here to tell you that, that’s not true. 

When I told my manager about quitting, I felt sick to my stomach with worry about how she’ll respond. She tried to convince me to stay at first, like all managers would but in the end she was just very happy for me, and everyone that I ended up telling had the same reactions. 

Don’t let fear stop you from going after what you want. 

Side hustling while working a 9-5?

So Tiffany, what type of conversation should people be having with their managers if they’re side hustling? 

First thing is to use your discretion.

Ask yourself, do they really need to know? 

What benefit will you have in telling them?

Is it something that they will likely find out about without you even mentioning it? 

And if so, are you okay with them finding that out? Or would you rather control that narrative and take more of a proactive stance of having it come from you?

Ask yourself these questions to decide if your side hustle is something that you even need to be telling your company. 

Make sure to also pay attention to timing, because perhaps you also want your side hustle to get to a certain threshold before publicly announcing it to your employer. 

If you’re just starting out, then I would recommend you position it more as a passion project, something that you’re just really motivated in, that’s a natural extension of your strengths or your core values.

The most important thing is to decide how you want to position your side hustle to the company. 

Never feel pressured to have to announce it on someone else’s agenda. 

Because this is your life. This is your career. 

And no one should make you feel like you need to do something that you, that you don’t want to do.

On that note, when that time does come and you choose, you want to tell your employer, be empathic and put yourself in their shoes.

Remind yourself that most employers will often think that your side hustle is going to take away from your focus on your normal work. So make sure to craft your communication to help them overcome and appease those concerns in the back of their mind. 

What’s your advice around non-compete clauses in contracts?

Especially if they might conflict with your side hustle?

Even though technically, whatever you do on your own time is your own time. Most companies will have a non-compete clause in their employment contracts. 

So you have to be aware of that. If you put yourselves in their shoes, it makes sense that they would have that because if your side hustle happen to be very similar to your corporate work then from the company’s perspective there is a concern of sharing competitive information. 

If you have any doubts about if what you’re doing on the side is overlapping, then I would recommend digging up and reviewing your contract or having a conversation with your manager directly.

You want to keep this conversation intimate and tight knit. 

I wouldn’t recommend going to HR right away. 

The reason I say that is because ultimately, at the end of the day HR works for the company. So HR will be looking at all the inquiries through the lens of, is this a risk for the business? 

Whereas, your manager will definitely know you better and be more neutral about this issue. At the end of the day, I hope that your managers are supportive of you and will see the genuine interest that you have in the side hustle that you’re pursuing. Maybe they’ll have a creative solution on how to make it work or ideas of how you should announce it internally without raising too many red flags. 

Bring it up casually with your manager first, maybe position as a side project that’s more for fun and get their input on whether this is something that can possibly post any conflict of interest before you get really into it. 

Even if you are very serious about this side project, it’ll be good to downplay it in the beginning. Talk with your manager to get more insight that will help you make more informed decisions until you decide your next move. 

What advice do you have for someone who wants to resign, but also don’t want to burn any bridges?

How much notice should you give? 

Firstly, I know that if you’re reading this article, you’d probably thought about quitting for a while. No one will just decide to quit on the day of. 

If you truly believe that it’s the right move to give your resignation, then do it with grace, respect and kindness. 

If you are a valued employee and if you’ve built solid relationships and really believe that your business is something you want to pursue full time, then go for it. 

Your employer will never stop you from that. Maybe they’ll be a little frustrated in the moment, but they’re not going to actually stop you. 

Second, you want to give at least two weeks’ notice.

If it’s a company that’s been generally really good to you and you know that it’s probably not going to be so easy to find a replacement for your position then you can also consider giving them even more time. 

Especially if you’re moving to do your side hustle full-time and not actually move to a different company, where there’s already a pre-decided start date. 

Try to give a little bit more runway if possible, because it’s a good courtesy to work out a transition plan with your manager and HR and leave things in a good order before departing. 

You can also offer to facilitate that transition process. This way you can show how much of an ally you are in this. Just because you’re leaving doesn’t mean that it’s all on your boss or your team to just figure it out. 

You can even suggest who can fill in your role. Or suggest a redistribution of work. 

Make sure to properly prepare where your files have been left off and what next steps would be right, this way you’re making your manager’s job easier and they’ll really be thankful for that. 

If you’re thinking to eventually exit and give that resignation, you can still get some last key wins under your belt. That will just help you leave on that much stronger of a note.

Remembering that just because you’re leaving doesn’t mean that you want to burn any bridges or sever the connections that you’ve made in your workplace. They can still serve as advocates for you and recommendations for you in the future. 

Tiffany’s own transition from corporate director to business owner 

Tiffany was someone who loved the corporate space and also killed it in the corporate space. She was in it for 12+ years and achieved 7 promotions in under 10 years. 

However, while she was on her second maternity leave she decided that maybe it was time for a chance and so she dived head in and started to work on her side hustle. Which was to help guide as many young professionals as possible to take control of their own career success as a career coach. 

Tiffany, being my ex-manager, had been following me on social media for awhile and that was around the time that she decided to invest in The BOSSGRAM Academy (BGA)

When she enrolled, she texted me and I was so excited we ended up hopping on a call to talk about her next steps. 

The aspects of BGA that she really found valuable was how actionable the lessons and exercises were. In the program, all the groundwork is laid out in detail so that all you have to do is do the work and follow it through to see results. 

I was so happy to hear that BGA helped her kickstart her side hustle, and gave her the confidence to leave her corporate job to pursue her business. 

Here’s what she had to say:

My favourite part about it was the Facebook community, because there you could always lean on others for support, encouragement, inspiration, even when difficult things came up. As a newer entrepreneur where you have a lot of those doubts or imposter syndrome, it’s amazing to just be surrounded by people who can really relate to what you’re going through. And it’s hard to really put a price on that.  

Then concretely through the methods that were taught in BGA, I was able to build an entirely new Instagram business account from scratch, which is now at over 4,000 followers in less than a year. I attracted amazing beta clients to start out, which then transitioned fairly quickly into over 20 one-to-one clients in my first year. 

And I’ve now successfully launched two rounds of my group version of my coaching program, where I’ve now impacted the lives of over 50 clients and counting 

Honestly, BGA exceeded my wildest dreams. And I was able to gain 40x times my investment in the program. 

Now I’m at the stage where I’m making what I did in my first year of business in the first quarter of my second year! So it’s just really exciting and I’m so, so grateful for that. I’ve always just been a big advocate of leveling up and acknowledging what you don’t know. So for me, BGA really filled in all the essential gaps that I needed at the outset of my business journey. 

If you’re reading this and thinking about transitioning in your career or starting something new. 

My advice for you is to just believe in yourself and your mission. 

Having the courage to just go for it is so important. 

Yes, there’s going to be ups and downs, uncertainty, mistakes, challenges, you name it. And when all of that happens, remember your initial intentions and your mission. 

Because that is going to be your driving force to achieve the greatness that you are destined to create in one way or another. 

Know that what you’re destined to do, IS going to bring a lot of benefit to others. 


Tiffany Uman Career Coach Profile headshot


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