Talking to your friends and family about being self employed is not always easy. But over the years I have it down to a science. Read my tips.

How to Talk to Family About Being Self Employed

With the holidays quickly approaching, it’s a good time to start preparing for holiday chit chat. Answering the endless questions of what you’ve been up to this year; what your plans on for next year. How is work/school? On repeat.

So if you’re like me, and are self employed, answering those questions can sometimes be difficult, especially to more distant or older relatives. But over the years I’ve learned how to tactfully talk to family about being self employed in a way that helps everyone understand exactly what it is I do all day. And no, it’s not all Netflix and sitting on the couch… well not always.

Sometimes the questions I receive are genuinely curious – what do you do exactly? How many hours do you put into that? But other times the questions are a bit more pointed – you actually make money from home? Are we talking real money?

At this point I generally laugh – because while I don’t always make as much as I did at my agency job in the past, there are some months where I make more (and some where I’m not even close). But I always make enough to pay the bills, and aside from money, I am happier – which is really worth so much in the long run.

So here is how I handle these situations.

Start by explaining your career path.

I make most of my freelance income as a graphic designer, so I generally stick to that. And I explain what it is exactly that I do as a designer. Even this part can be tricky sometimes without adding in the working for myself aspect. But I try to explain in a couple of sentences and then pause for further questions. Or for them to decide that now is the perfect time to grab another drink… and then I’m off the hook!

Break down your day to day.

Next, talk about how your career breaks down into your day to day tasks. And here is where I start to incorporate how all of this is done from home (or the coffee shop down the street, etc). Sometimes I even share what my top to-do items are for my upcoming week or month.

Share your recent achievements.

If the conversation is still going strong, now is when I generally pull out my phone. I’ll show them my portfolio site, or pull up a recent web design I’ve worked on. Then I start to explain how those visuals were created. If you’re a blogger, you could even pull up your blog – unless of course you don’t want your family reading it. Then now is when you grab another drink…

Chat about others in your field who are also self employed.

If you don’t want to self promote the whole conversation, or if you’re still being questioned, sometimes it helps to bring a third party into the mix. Show off someone else’s work who you admire, and who is also making a living in the same way you are. This will make your work seem more relatable.

Share why you want to be self employed.

For me, this means so much more flexibility. Yes, I’ve had days where I’ve worked 16 hours. But I’ve also had time where I’ve decided a day before that I’m packing up and going on a quick road trip – and then I work a few hours in the evening from our hotel room. I also want to start a family soon and my freelance will allow for me to be home during the day but still bring in income, and have my own identity outside of being a mother.

What if that doesn’t work?

Well then you have a few choices. You can make up a new story for each person who asks. Grandma thinks you’re a doctor now and Aunt Susie thinks you’re going to be in the next superhero movie? Sure!

You can print out a sheet ahead of time to pass around the party that goes over all the general questions – and even “hints” at what you would rather talk about aside from work.

You can pretend like someone from the other side of the room is asking for you as soon as anyone asks.

Or you can simply say you don’t want to bore them with the details, but you’re happy and making money and then change the subject.


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Talking to your friends and family about being self employed is not always easy. But over the years I have it down to a science. Read my tips.Have you ever had trouble explaining your career choices to family?

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34 Comments

  1. Worst case scenario, tell them you run a sex ring out of your home.
    WHAT??

  2. I’ve worked as a freelance writer and travel blogger for almost two years now, and some of my relatives (mostly the older ones, like you mention) still can’t figure out how I make money on that newfangled thing called the internet! They’re mostly positive, if a bit clueless. The people who I see constantly–my parents, my husband, my sister–have been nothing but supportive and amazing, and they keep me going! 🙂

    • I’m glad to hear you have support! My close relatives are super supportive too which definitely helps! I love when I first have to explain what a website is before I can explain that I design them ha

  3. I dread having this conversation with people who just don’t get it. I’m not sure if I will ever be truly self-employed, but I feel like I am right now with my blog while I’m in grad school. A lot of my fellow cohort members don’t get why I just don’t work!

  4. Great tips! I’m not fully self-employed yet, but I do have a hard time explaining to people how I earn money from blogging and freelance writing.

    • Thanks Chonce! Even when I start to make a little from blogging I think I’ll leave that part out so I don’t have too much to explain lol

  5. I love the part of sharing your recent achievements. I feel like once you have kids it’s more easily justified being “self-employed” but it shouldn’t have to be that way! This is a great post. Holidays can be wonderful and stressful at the same time!

  6. I hate explaining self employment to people! Especially older people. They just don’t get it. It got to the point where I developed a speech about what I do but in general they still seem suspicious that someone can work from home.

  7. I already get some surprise from working part time (outside the home) so I can’t imagine the disbelief I would get from stating I’m self employed! My parents were self employed but they owned a deli – self employed working on the internet would indeed be harder to explain!

    • My parents own their own company as well so I think that has helped a bit – but the fact that I do it all from home seems to be harder to swallow. And that I don’t really have any employees.

  8. I’m lucky in the fact that many of the relatives we see over the holidays are also stay-at-home-moms or work-at-home-moms. I don’t even bother explaining my blog to the older relatives because they have no idea what I’m talking about.

    • I love that you have family that is in the same position as you! I don’t have any cousins on my side and my husband’s cousins are in very different positions than us so we always seem like the odd ones – me especially lol

  9. This couldn’t have come at a better time as I recently started working from home and am about to see the in-laws for the first time… while dreading it you’ve given me some good points to start with. Thanks for the tips.

  10. YES to this. Thankfully, both my family and Kyle’s family are super supportive of everything we do so it hasn’t been a huge issue to explain why we move so often or why we chose our career paths. I say more power to ya if you can make money at home! There are give and takes to everything in life and if you’re happy, then who cares if others understand 🙂

  11. A while ago I saw an article about a teenaged girl who literally printed out a sheet for a family event so people wouldn’t keep asking the same questions, which while totally sassy, I thought was genius!
    I will admit, I don’t really talk about blogging (my “work from home”) while I’m out, but occasionally my husband brings it up to people while we’re out and I do feel a little funny explaining myself!

    • The print out sheet isn’t something I would do, but it cracks me up that it’s happened before. And I would totally respect why someone would do that haha.

  12. Love this! It can be really difficult to explain what you do as a freelancer, especially blogging. Most people don’t understand you can earn money off of ads and partnering with brands. These are great tips, though!

  13. Rae

    People have no idea how focused you have to be in order to be self-employed!

    • I totally agree! And when I tell them I actually work more hours than my husband does they usually look at me like I’m nuts haha

  14. What a very good subject to write on. That is very helpful, I need to learn some of those tricks of explaining.
    Kathleen
    Fridays Blog Booster Party #30

  15. Sam

    This is so incredibly helpful. As I start thinking more and more about moving to this work from home sector to be with my daughter and do freelance engineering, I’ve often thought “what will people think of me? how will I explain what I do and how will I figured out a way to do it that sounds credible…important…?” I really liked this advice. Breaking your day down might even help the person who is self-employed feel more empowered, like they have a defined schedule and how they are spending their time is valuable. Awesome & thanks for linking up with us at Welcome Home Wednesday this week.

    • It definitely helps me explain it – right now without kids I feel like people really have no idea what I do. But when I have kids, I want to keep working – and it would be nice if at least my extended family understands I still work ha

  16. Hil

    Mine are more on working from home and being an independent contractor, but people are more focused on the fact that I am a mom at home with my kids and forget I work too.

    Thanks for sharing at Turn It Up Tuesday

  17. Thanks for entering this in #ThePinterestGame! Good luck!

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