Leaving Your Job for Coaching? How to Win Over Your Family

Last week, I was in a session with a client about to leave her 6-figure job as a consultant to run her own coaching business. The session started with another goal in mind, but it gradually led toward how her family didn’t understand her perspective and didn’t support her.

She broke down.

Her family’s approval was super necessary to her, but it was also causing tons of friction inside her and causing her to lose confidence in her skills as an entrepreneur.

She’s not the only one going through such a situation.

I went through the same problem almost 2 years back, too, and it took 1.5 years to convince my parents that I could do it. And while the situation gave me clarity on what I wanted, the period was horrible.

I’ve met so many other folks who undergo similar problems too! I don’t mean to be biased here, but in my experience, especially women.

Transitioning in itself is terrifying and challenging. Friction with family only makes the fire burn bigger. That’s why I wanted to focus on this topic, hoping it’ll help you if you’re going through the same situation.

Disclaimer: Our parents, partners, and family always wish us well and are concerned about us (mostly). They’re just scared for us and think of the worse scenarios. Unless and until we deal with it with empathy, the scenario will only lead to unrepairable breaks in the glass.

Hopefully, the below tips will help you communicate with them and make the transition smoother. Let’s begin!

1. Work on your side hustle for at least 6 months before approaching them

This step is to prove to yourself and them that you’re not in this for the short term, nor do you make rash decisions (like quitting your full-time job) without thinking things through. Once you’ve done it, they’ll at least know that you’re somewhat serious about what you’re doing.

Trust me. I made that mistake. 2 months after I started writing, I announced to my family that I was leaving my well-paying job to become a full-time writer. Yeah…that road didn't go well when I hardly earned $20 per month🙈.

If your “passion” fizzles out before six months, you are unlikely to pursue it in the long run, so you don’t have to go to them at all. Or if you want to continue it as a side hustle for a longer time, too, it usually doesn’t become a problem.

2. Make a list of all the questions they can possibly ask you

This is the most crucial step of all.

Picture the conversation in your head. How do you think they would react when you approach them with your decision? What are the questions they’ll ask? What would be their concerns?

Write all of them down. Plan the possible scenarios, and write the answers down. Do they make sense to you? I know this seems like a lot of planning and plotting, but it does impact their lives, too…so it’s good to have honest answers.

Mind you. If they don’t make sense to you, then it means you’re not convinced enough yourself. It doesn’t really make sense to approach them then because you’re unsure of what you want to do. Be truthful to yourself.

Some of the questions my parents and husband asked were:

1. What’s your plan going forward? Do you at least have a one-year plan?

2. How are you going to manage your finances?

3. How much money would you need to invest in starting your career? Further studies, courses, websites…so on and so forth.

4. Did you discuss it with your partner? [my dad asked this 😅]

5. How many coaches have you reached out to? Have you asked them what this career entails? We want you to do your research when you take the plunge.

Only you would know your parents. But the most common questions, I assume, would be the finances and one-year plans. So have an approximate idea about it before you approach them.

3. Understand their fears and concerns

I used to be a rebel and considered my parents enemies who didn’t want me to achieve my dreams. Yeah…I can go a little extreme sometimes.

But then, when I had logical, heart-to-heart conversations with my mother, I realized her fears weren’t wrong. Apparently, during college, I suddenly came up with extremely vague career paths, such as food journalist, librarian, etc. Vague because it was sudden, I wasn’t serious, and I didn’t have any plan.

Those “dreams” fell off the wagon in a few days. I was always known to be impulsive, so my mother didn’t want me to take massive, impulsive risks with my career too.

Moreover, she knew that one of my life purposes was to be financially independent. So when I switched to writing (I initially set out to become a writer), my income would take a hit, which she feared would give me ego issues.

And thinking about it later, I realized there is a high probability of that happening (that did happen)

Your parents and partners know you better than you do yourself sometimes. So listen to them. Understand their fears and consider their points. Don’t turn on your defensive mode immediately, and shoot back. They only wish you good [mostly].

4. Please show them your world

One primary reason many parents were against creative careers was because they had no idea about that world or what it entails. They were only aware of the stereotypes that surround such jobs. And, of course, most of them weren’t great.

For example, When my friend told his parents he wanted to become an actor, they immediately responded, “Please don’t get into drugs.” Looking back, we laughed about it, but their fears were legit!

In my case, I had to sit down and explain the career options which come with writing and coaching, invite them into my world, hold their hand, and make them familiar enough for them to believe that I can sustain here, provided I put enough effort into it.

5. Share your vision, passion, and goals

Why do you want to transition in the first place? What vision do you see for the world? What impact do you want to create? Why are you so passionate about this?

Even if it’s for selfish reasons, as it was for me, it’s okay (I wanted freedom of choice and money, which wasn’t possible in 9 to 5)

All this will make them understand why this transition is essential to you and allow them to empathize.

I made my parents realize they had educated me and made me independent enough to think beyond money. That I had the confidence to be successful. I simply needed some time:)

6. Lastly, set some boundaries

When I initially quit my job, I asked my slightly intrusive family to give me space. Not ask any questions until I settle down in the new role.

It might be entirely different for you.

Most of the time, you can’t convince them in one conversation (of course, who are we kidding). And you might have to put your foot down in that period to save your sanity. It’s not always flowers and petals, you see?

I’m sure you’d understand if you’ve Asian parents.

This is a fine line to thread on. To not be snappy while protecting yourself during the time. Once my parents saw my conviction in what I wanted to do, they started accepting things.

You do you. Find your balance. Find your boundaries.

Why do we need to discuss our careers with our parents/partners and convince them of the same?

Good question.

One, they’re family and will always wish the best for you (in most cases). Second, you get to channel the numerous experience that you have at home. Get a different perspective. Your parents would also have crossed their 20s like you, and they would have taken risks, fallen, and risen from their mistakes. Now, when you’re taking the leap, they can advise you on the highs and lows of life for you to use as you move forward.

You also cannot put a value on the support you get from your partner or parents. Today, my mom sends me meals if I’m too busy to cook, and my dad has already started researching taxes for solopreneurs. It’s heartwarming to see them support me in their own way. I also discuss all my business decisions with my husband to get his perspective.

Most importantly, they’ll be one of the few people who will hold and support you when you fall. They might say, “I told you so,” but they would still hold you.

Disclaimer: Not all parents accept our paths. I know friends who have friction with their parents years after too. We cannot help but stay firm and prioritize our dreams. You have done your best, so don’t beat yourself up about it. 

Time for some personal rant!

I took some time off for 2 weeks and went on a 1-week beach vacation! Finally! I was looking forward to it for months, mainly because of the surfing lessons ♥️

I failed miserably, by the way, and almost got drowned 4 times with a 6-feet wave hitting splash on my face giving me a migraine for 2 days.

But it was all worth it.

I turned 26!!!!!!!! And witnessed the best sunset I could ever have on that day…it was beautiful!

Initially, I was guilty of not publishing the newsletter for 2 weeks, but then I realized I needed to take my own advice…I have to run my business my way😅. I felt fucking good later, so it was all worth it:)

I’m back to work with full force and have something cooking behind the scenes. I’ll keep you guys informed by next week! It’s gonna be awesome!

Here’s the amazing sunset bdw…

Until next week,Shruthi