How To Talk To Your Family About Working For Yourself

by stephen warley

When you decide to start a business, one of the toughest and most unexpected challenges you may face is how to talk to your family about working for yourself.

Believe it or not, one of the most common questions I receive from our community has nothing to do with starting a business!

I’m often asked in varying ways, How do I talk to my loved ones about the work I want to do?”

You may be super excited about making this big change in your life, but talking to your loved ones about it makes you feel very apprehensive.

Why?

You’re afraid they won’t understand.

You’re afraid they won’t support you. Worse, they’ll doubt you!

You’re afraid they will judge you and your business idea.

You dread questions they might ask like:

  • So how’s work?

  • What are you working on now?

  • How’s your business?

  • Are you making any money yet?

It’s especially tough hearing those questions in the early days of your business when you don’t have everything figured out.

Not having answers to those questions makes you feel like you don’t know what you’re doing.

Those questions make you feel judged. 

They remind you of your own doubts too.

The hardest thing about working for yourself is coming to terms with your new identity.

You’re shedding your employment identity to give life to your new identity as a solopreneur.

The way you view your attention, energy, time, money and relationships is going to change dramatically.

When you make such a big change like this in your life, how others perceive you will change too.

You’re nervous about talking to your family about working for yourself because you’re afraid it will change how they see you.

You’re afraid you might lose them because they won’t like the “new you”.

All you want is to feel supported and understood by those you love the most because you already feel so vulnerable about making this decision.

But what do you do when your mom or dad or wife or husband or best friend just “don’t get it”?

How do you talk to your family about working for yourself when you feel like they might be critical of your idea or even try to talk you out of it?

First, I know this might be hard to do, but remember they love you.

What you might be receiving as judgment and criticism is their way of “protecting” you. More often than not, they believe they are acting in your best interest because they don’t want to see you get hurt financially or emotionally.

Your loved ones are your first investors. They might not give you money, but they can provide emotional support.

Give them the time and space to understand what it is you’re creating. Try to use language and analogies they understand.

And from my experience, it’s going to take more than one conversation. Look for opportunities to share what you’re doing over and over again. Do it in a way that aligns with their interests.

Your family’s reaction to the work you want to do says more about their own fears about starting a business than doubting your ability to do it.

Over time, as your loved ones see that you’re financially secure and happy, they will tell you how proud they are of you!

Second, they aren’t critical because they don’t believe in you, they’re just unfamiliar with your idea or way of working.

My parents still have no idea what I do after 25 years of working for myself! Working online from anywhere in the world is so far removed from what they were taught about how to earn a living.

When someone is unfamiliar with something new, they’re understandably going to have a lot of questions. Calmly answer them.

Try your best not to take their questions personally.  Again, they’re reaction has more to do with their own issues than your abilities.

Third, they’re envious of you.

Many of your harshest critics take out their own self-doubt on you.

They would love to do what it is you are doing, but they have convinced themselves they can’t do it.

We all have an inner critic.

While you’re choosing to put your inner critic in its place, people close to you are allowing their inner critic to unknowingly rule them.

Finally, build a new family of support.

As you continue to transform how you work, you’re going to need support from like-minded people to motivate you and encourage you.

You may not get the support you’re seeking from your loved ones off the bat, so start building relationships with people who are excited about your plans.

I like to think of my closest supporters as my “adopted entrepreneur family”. I have intentionally chosen them and they have chosen me. Our values are aligned.

I still love my own family very much, but have realized long ago, they support me differently, but love me no less compared to when I was employed.

Are you still struggling to find your new entrepreneur family?

Consider joining one of our Communities of Practice.

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