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One of the scariest parts of quitting your 9-5 can be telling your friends and family. Many of us dread it as much (or more) than telling our boss! It doesn’t have to be a bad experience, though. There are some things you should know before you tell everyone the news, from practicing your answers to having a support network in place. Let’s dive in!

How to tell your friends and family you're quitting your day job

Be Prepared for Questions

Questions are inevitable. They’ll likely be a mix of positive and negative, and that’s okay. Just know that they WILL come.

Think about the kinds of questions that you would ask someone who was changing careers. Start making a list of those questions so that they don’t come as a shock when someone asks YOU the same question. Being prepared will make the answers flow more smoothly and make it clear to the other person that you really have made an informed decision. If their concerns are eased right away, they may even ask fewer follow-up questions!

Homework #1:

Make that list of questions! Think about what Grandma will ask you. What will Aunt Jane want to know about your next steps? Make sure to come at your brainstorming from someone else’s perspective rather than your own so that you can address their concerns.

Understand the Other Point of View

Speaking of the other person’s concerns, try to see things from their perspective. If someone is criticizing your decision, there is bound to be a reason behind it.

Maybe they have tried entrepreneurship in the past and failed miserably. Someone else they know could have made the entrepreneurial leap, and even the second-hand experience could have been enough to give them pause. This prompts genuine concern because they don’t want the same thing to happen to you.

Another motive for questioning you could be jealousy. Think back to before you decided to quit: were you jealous of others who were of the rat race? If the person you’re talking to hates their job or career field and wants to leave, it could make them rude or petty, even though they want you to succeed. If you think this is the case, try walking them through the process you went through. Help them to see the steps you took and maybe you’ll open some doors for them at the same time – win-win!

Homework #2:

Think about the different backgrounds that you may encounter in your friends and family. Do they know someone who failed in entrepreneurship? Have they worked for the same company for 20 years and can’t imagine why anyone wouldn’t want that kind of stability? Maybe they just plain don’t have any idea how entrepreneurship works!

Make a list of these points of view and try to understand them before you tell your friends and family about your career pivot. If there’s someone in particular that you’re afraid to tell, sketch out their specific background and try to see this change through their eyes.

Practice Your Answers

Remember that list of questions you made? Take that list of questions and ask someone who already knows the situation and supports you to help you practice your answers. It’s essentially like preparing for a quiz back in school, but (hopefully) more fun!

If you have your answers at the ready, you won’t have to worry about being caught off-guard. Even if the questions that are asked aren’t exactly the same as the ones you listed, your answer will be able to roll off your tongue more easily since you have something similar already in the back of your mind.

Homework #3:

If your practice partner knows some of those friends and family members that you’re worried about telling, ask them to roleplay those specific people. This will help you feel even more confident when you tell them! Practice more than once, too, so that you’re ready with your answers when the questions come.

Build a Support Network

Hopefully you have some local friends or family that are understanding of your entrepreneurial leap. Even if you do, though, having a support network of other entrepreneurs is still vital. It can be hard to fully comprehend the day-to-day challenges that come with entrepreneurship if you’re not in that world yourself. One of the best things you can do to put yourself in a position for success is to surround yourself with positivity and other entrepreneurs!

Why you need a support network when you quit your 9-5

A great place to start is your local Chamber of Commerce and SBA (Small Business Administration) office. They often have in-person events and networking opportunities. You can also find a mentorship program and maybe even inquire about starting or joining a local entrepreneur mastermind group. Meetup is another great resource for finding local entrepreneurial groups that you can join.

Maybe you’re like me and live in the middle of nowhere, though. It can feel very lonely when the closest fellow entrepreneurs are an hour or even several hours away from you. Never fear, though – we live in the age of the internet! One of my favorite networking and support outlets are Facebook groups. I’ve made connections through these groups and Twitter chats like #createlounge, and I met some of my best business friends online.

Whether you build your support network online or offline, make sure to be active. Not only can this help you grow your business, but when times get tough and you’re feeling discouraged, these groups can provide a sympathetic shoulder to cry on and give you advice on how to address the situation. Never discount the value of having others around you who are in the same boat or have been there before!

Homework #4:

Make a direct connection with at least two other entrepreneurs. They don’t have to be fresh off the block – you can connect with people who are at different stages in their business as well! If you’re stuck, shoot me an email and I’d be happy to chat. Maybe we’ll connect, and if not, I’d be glad to see if I know anyone who might be a good connection for you. I would also love to send you some invites to Facebook groups that I enjoy networking in, so feel free to reach out!

Just Do It!

What it all comes down to is that you have to just steel yourself and do it. Waiting just makes things feel worse in the end, and you may be surprised by the outpouring of support from your friends and family! Even if they aren’t standing behind you with banners and pom-poms, it’s still better to get it over with.

If you wait until after you’ve quit, your friends and family may feel like they’ve had the wool pulled over their eyes. Even if you’ve been waxing eloquent over how much you hate your job for months, it may still come as a shock to them. Loop them in earlier than later and you may even find that some of them have some great advice! Take all the comments and well-meaning advice with a grain of salt, of course, and don’t let any naysayers discourage you if you’re sure this is the right path for you.


If you’re prepared for the inevitable questions and understand where your friends and family are coming from when they ask, it will make things flow so much easier. Practicing your questions with a trusted supporter and having a support network in place will help you feel more confident as you begin to share your exciting next step. Don’t let the fear of discouraging reactions stop you from taking this crazy awesome leap into entrepreneurship!


Are you ready to shout it to the mountains that you’re quitting your 9-5? Maybe you’re a little more hesitant. Tell us in the comments! We’re here to cheer you on.

How to Tell Friends and Family that You’re Quitting Your Job
The Creative Entrepreneurs L.A.B.