Considering self-employment? Start with these 4 conversations


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“Honey, I’m thinking I should quit my job and work for myself…what do you think?”

When you’re self-employed, you don’t operate in a vacuum. There are other people—like your partner, your children, and even your current employer—who will be impacted by your decision.

If you’re considering self-employment you know it’ll be a major shift, not only for you, but for those closest to you.

Because of the impact self-employment will have, it warrants some thoughtful conversations with the people who matter most to you.

Here is a brief overview of who you should be having these conversations with, and how to handle them.

While this is by no means a comprehensive list, it’s intended to get you started.

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1. Your spouse or partner

Your spouse or partner will be the most impacted by your decision when you’re considering becoming self-employed. In fact, it’s best to have this conversation well in advance of when you leave your existing career.

Transitioning from employee to freelancer means losing your health benefits, your employer matched 401k, potentially a reference, and most importantly, a steady paycheck.

It should also be noted that in a recent study by QuickBooks Self-Employed it was found that 1 in 3 families have had to make financial sacrifices. This is not meant to be discouraging, but rather a reminder of the gravity of the decision to become self-employed.

This is a life-altering decision and a shared effort between you and your partner—not something that you surprise them with after you’ve already taken the leap.

“Transitions are tough, no matter what. The best way to survive as a couple is to approach it as a joint venture. Both people are going through the changes,” explains Rebecca “Kiki” Weingarten, transition coach and co-founder of New York City-based Atypical Coaching, in an article for The Chicago Tribune.

How to Handle This Conversation

Starting this discussion can be nerve-wracking. Do it early—ideally, when your brain first starts churning on how to become self-employed.

Make sure that you strike up this conversation in an appropriate environment. Find some quiet time when it’s just the two of you, so you can give the topic the attention and consideration it requires.

Be prepared for this to be an ongoing, sometimes emotional conversation. There are concerns and harsh realities—from finances to benefits to work schedules—that you and your partner will need to work through together, that can’t be resolved in a single conversation.

When reports show that finances are the leading cause of stress in relationships, it’s crucial that you and your partner make a habit of having those conversations together.

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2. Your employer

When you sit down with your manager to submit your resignation, you’ll be met with an inevitable question: Where are you going?

This is a tough question to address, and even tougher when you aren’t moving on to another traditional 9-5.

Needing to explain that you’re going to start your own business can stir up plenty of self-doubt. Leaving the predictability of a steady paycheck can make you and your boss feel like you’re doing something crazy.

How to Handle This Conversation

As anxiety-inducing as this talk might seem, remind yourself that this is business.

Believe it or not, a whopping two million Americans quit their jobs every single month. So, while you might feel guilty for leaving your employer, it’s not out of the norm.

As tempting as it can be to spit out self-defeating statements like, “This might be crazy…” or “This probably won’t work out, but…” resist the urge to diminish your decision. Explain that you’re becoming self-employed and that you’re excited to see where it takes you.

You may be surprised by how supportive your boss is, and congratulates you on your bravery.

Finally, remember to express your gratitude for the opportunities that job gave you. Don’t burn any bridges; you could end up doing some contract or project work for that employer in the future.

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3. Your children

Whether your children are young or old, your decision to become self-employed still impacts them.

If your children are younger, it’s best not to speak with them about your career change until you and your partner have made a firm decision with a timeline and transition plan in place. This is an adult decision, and you don’t need to stress your kids out with the logistics.

If your kids are already grown, they can be a great sounding board—particularly because their opinion likely carries a lot of weight with you.

How to Handle This Conversation

If your children are out of the house, your decision to pursue self-employment still matters.

With grown children, explain that you’re seriously thinking about self-employment, and ask for their thoughts on that decision. There’s a lot that goes into running your own business, and having a fresh perspective from someone who’s known you all their life certainly can’t hurt.

The most important thing to remember when discussing this with young kids is that you need to make the impact on them clear. “There may not be any new toys for a while” or “We might not go out to eat as much” or “I’ll be home more, but I need time to be working” are conversations they can understand. It may sound brutal, but it’s important they understand how this will affect their lives.

Science has proven that kids are programmed to be selfish, since it takes time for the considerate portion of their brain to mature. To have a productive conversation, speak their language and let them know what changes to expect.

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4. Other loved ones

Your immediate family and your existing employer will be the ones most directly impacted. However, there are still other loved ones—such as your parents and other family to your close friends—who you’d still like to loop into this life changing decision (especially if you ever have to borrow money.).

Going back to the QuickBooks Self-Employed study from before: 4 in 5 have had to miss a social event at least once in a year, which can be hard for anyone who’s used to having you around often.

How to Handle This Conversation

Though keep in mind, this shouldn’t be treated like an investment pitch.

Even the most supportive and encouraging of loved ones will feel taken advantage of if you brief them, and immediately launch into asking for resources or financial help.

Treat this discussion as an honest chance to update your loved ones on a big change because you care about them—not because you need something from them.

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Tackling the personal side of becoming self-employed

Figuring out how to be self-employed is challenging, and so much of the advice around entrepreneurship centers on the business side of things—like accounting, taxes, inventory, hiring, and those other logistics.

It’s important to remember that even though this is a personal decision, it has a ripple effect beyond just yourself. It might be called self-employment, but nobody ever does it alone.

Make sure to have these important conversations with the people who matter, and you’ll move into your self-employed life with plenty of support.

This article originally appeared on the QuickBooks Resource Center and was syndicated by

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