032: How to Get Your Family On Board With Your Dreams

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It is exponentially more difficult, nearly impossible even, when you feel you don’t have the support of your family. Sometimes that lack of support is explicit, while other times we worry they wouldn’t understand and in our fear end up creeping into a cycle of guilt and frustration about making time to pursue our dream.

In this episode, we talk about some practical ways you can communicate your desire to pursue your dreams in a way that will help your family be on the same page with you and supportive of your dreams.

Highlights, Takeaways, & Quick Wins

• Glean what you can from what your family has to share.
• As long as you’re not harming someone else in the pursuit of your own dream, you should go for it.
• You may need to scale back the amount of time you spend around negative influences.
• When you’re pursuing your dream, your family gets a better version of you and everyone benefits.
• Allow your significant other space to say what they feel about your dream.
• Don’t pursue your dream at the expense of relationships or sustenance.
• Come up with a rough version of a business plan to share with your family./li>
• Agree on a plan for when and how often you’ll work toward your dream.
• Schedule time intentionally to keep your family on the same page.
• Establish expectations with your family.

Show Notes

• 03:14 Ben: When today’s topic first showed up in the schedule, there were a few people in the chat who expressed their excitement that we were talking about this topic. They’ve gone through the experience of either trying to get their family on board with their dreams and struggling, or feeling nervous about sharing their dreams with their family because they’re worried about how they’ll react. This will definitely resonate with folks. There were several people in the chat today who had questions about this, and we’ll get to those later.

Extended Family

• 04:04 When I talk about immediate family I mean a spouse or kids, if your pursuit of your dream affects them or their schedule. Extended family is also on people’s minds, like their parents, brother, sister, uncles or aunts, whoever is in your life and cares about you and wants the best for you. They may have an opinion about whether or not you should pursue a dream. Growing up, I had many voices in my life who wanted good things for me. They wanted me to be safe and happy. Out of their desire for those things for me, they would share their thoughts and opinions about what I should do with my life. As a grownup, that didn’t stop. That’s the case for most people. Did you experience that, Rachel?
• 05:26 Rachel: I was raised by a single mom, and she was always very supportive of whatever I wanted to do. She recognized even before I did that writing was something I wanted to do. I come from a different circumstance. I didn’t have a lot of pressure to perform, but I put that pressure on myself. There have been times when my mom has said, “What are you going to do for money?” I know where she’s coming from, and it’s not meant to discourage me. She’s genuinely concerned.
• 06:27 Ben: What stood out to me about what Rachel just said was her mom’s question, “How are you going to make money?” Sometimes, questions come across as a lack of support or skepticism that you’re going in the right direction. Maybe you’re indebted to that family member or those family members in some way—there’s legitimately something you owe them that would prevent you from pursuing your dream at that time.
• 07:07 Rachel: Do we ever owe our parents something?
• 07:10 Ben: It depends. There’s a whole other conversation to be had on family values around lending and borrowing money and resources. Hopefully, that’s not the situation you’re in.

You don’t owe it to your family to follow your dream the way they think you should or to not do it because they don’t approve.

• 07:45 You’re not obligated to adhere to their wishes for you. You can do your own thing. What can be a benefit to you, and what you should definitely do, is let them know that you love them and that you appreciate their concern and their desire to share from their experience and wisdom. Glean what you can from what your family has to share, because they have gone through experiences. Allowing them to tell their story gives you more context so you can understand where their message is coming from. Hearing, “What are you going to do about money?” in and of itself, might seem like a deterrent. Understand the backstory—“Oh, when I graduated from high school, I had to go out on my own, and I was trying to go to school and work a job, and I ended up getting really bad grades and having a hard time…” Getting the story gives you context, and it helps clarify where that’s coming from.
• 09:00 Most of the time, what your family really wants for you is safety and happiness. It’s hard for them not to define that for you based on their own experiences. When it comes to extended family you are your own person, and as long as you’re not harming someone else in the pursuit of your own dream, you should go for it. Honor those relationships as much as you can, but be respectful. Don’t say, “Forget you guys.” You may need to limit the amount of time you spend around those family members because of their limited thinking, because that can rub off on you. At the very least, you need to offset the time you spend around those influences with influences that will pull you in a positive direction.

Family relationships are important, but if they’re hindering you from pursuing your dream, you may need to scale back the amount of time you spend around those influences.

• 10:26 Rachel: The more we believe in what we are supposed to do, the less those opinions will matter to us.
• 10:36 Ben: It can be hard if the only voices in your life that really mean something to you are unsupportive. You’ve grown up with these people who have protected and guided you, and most of the time, they steered you in the right direction. You trust them. It’s difficult, with that kind of relationship, to think differently, unless you have other influences you’re allowing to speak into your life as well. Believing in yourself and your ability to achieve your dream, some people just have that. They say, “I don’t care what the rest of the world says. I’m going after this.” If the only voices in your life are saying, “I don’t know. That seems like a long shot,” then you need to get other voices in your life that will foster that belief and confidence.

Immediate Family

• 11:38 When I say “immediate family,” I’m talking about your spouse or your partner, where the decisions you make really influence the other person. This includes your children, especially at an age when you pursuing your dream could mean something they have to sacrifice. I see two possibilities here. There’s the scenario where they’ve explicitly said, “I don’t agree with that. That’s not something you can accomplish. I don’t think you should do that.” It’s very clear and there’s no ambiguity. The other scenario is where you haven’t had that conversation, but you feel guilty when you’re pursuing your dream, because in the back of your mind, you think, “They probably don’t understand what I’m doing. It may look to them like I’m doing this at the expense of my family.” You may be projecting your own fears of what might happen onto them.
• 13:28 I want to talk first about the scenario where there has been communication, and it has been negative. The foundational belief that should guide how you deal with this situation is this—you are the best version of yourself when you are pursuing your dream. Your family needs the best version of you. It’s good for them. It’s not just about you and your personal fulfillment. When you’re pursuing your dream and living into your potential, your family gets a better version of you and everyone benefits. You have to believe and take hold of that. Then, every conversation after that is going to be in service of what is not only best for you, but what is best for the family. Open up communication. First, reinforce the relationship. Let your significant other know, “I value our relationship and I want it to be strong and healthy.” Make sure they understand that it’s not just about you, but that you pursuing your dream is good for your family as a whole. It’s a good thing for the relationship you have with your significant other.
• 15:26 Rachel: Speaking from our experience, how do you approach the issue of who is going to be the supporter while something is being built?

Pursuing your dream is good for your family as a whole, but not at the expense of relationships or sustenance.

• 15:57 Ben: There are a variety of different answers to that. You do need to be able to pay your bills. If there’s a conflict between being able to pay your bills and being able to pursue your dream, then working toward your dream looks like making sure paying your bills is taken care of so you have at least enough margin to spend time pursuing your dream. That season may look like spending all of your time growing in your day job or making your time more valuable so you can scale back on the time you’re spending doing these other things. It’s okay for pursuing your dream to look like that, but don’t say, “I don’t have to worry about making money anymore. I’m going to go after this, so that’s your problem now.” It’s the same with relationships. If pursuing your dream means that you won’t have any time to foster meaningful relationships with the people closest to you, it’s not worth doing.
• 17:11 Rachel: The communication between spouses is really important. We reached a time in our dream pursuit where we were in a band together, and all of the guys quit their jobs, but we had a baby number two on the way. It wasn’t that Ben wanted me to stay at the job, but for my own security reasons, I needed to stay at that job. We didn’t really talk about those things. I was there for eight years, six after that. I started not being myself. I was almost dying inside. Not only was I holding a full time job, but we were pursuing something on the side and I was trying to be a mother and keep up with all of the home stuff. It was really tough. I’m not great at saying, “There’s a problem. I need this fixed.” I’m so conflict-averse that I’ll do what needs to be done. Foster that communication and make a safe place for a spouse to be honest about those things.
• 18:54 Ben: We can have this tendency to say that we want to hear what the hangup is, but we don’t really want to. “Well what’s your hang up?” The other person will think, “If I tell you what my hangup is, it sounds like you’re just going to be angry with me.” It’s so important for us to allow our significant other the space to say why they feel whatever they feel about your dream. Empathize with that and seek to understand how they’re feeling. Acknowledge that you understand, show them that you’re empathizing with them, and then try to work that out. If you never do that, you never address their problem. There may be a simple solution, but you’ll never know unless you get to that point. You won’t get to that point if you’re not giving them a safe and comfortable space to express those things.

Addressing Conflict

• 20:09 Cory says, “My family is pretty supportive, but there have obviously been some scuffles here and there. I usually find that it’s about the things they don’t really understand or used to want for themselves, but were never able to get it. By us living our dreams, it’s almost like remembering they weren’t able to.” Sometimes, the problem you assume they have is not really what’s going on. It’s so important to have those conversations. There are two possible outcomes in this situation. One is that they’re willing to continue the conversation. Once you’ve expressed understanding and addressed their concern, you enter into a negotiation phase.
• 21:00 Rachel: You’re talking about when spouses are talking?
• 21:02 Ben: Yes. You’re in a negotiation stage, and that’s what we’re going to talk about next. They might become indifferent and say, “Well, you do whatever you want.” Be really careful about that. That can be a trap. Indifference is almost always not really indifference. You don’t want genuine indifference—you want the fight, because what you really want is for them to be on the same page and supportive. Either you didn’t convince them that you understand how they feel, or you didn’t come up with a good enough solution to the issue. If they’re indifferent, I would drive them back through that process. Do this delicately.

If you believe your dream is a good thing for you and your family, then it’s worth fighting for.

• 22:43 Don’t fight in a way that destroys your relationship, but in a gentle and persistent way. If they give you some kind of an ultimatum, this is the really hard thing. My best answer is that the commitment you made to that person needs to be more important than following your dream. That’s based on our personal beliefs and experience. If Rachel came to me and said, “Ben, I know you really love music, but I can’t let you do it anymore.” I’m going to stick with this relationship because that’s the commitment I made. I hope that through our communication and our relationship, as we grow together and she sees the symptoms of me feeling sad and unfulfilled because I’m not able to do the thing that I dream of doing, that she comes around and realizes that this may be a conversation we need to reopen.
• 24:01 I hesitate in prescribing that as the answer for everybody, so that’s something you’ll have to wrestle with for yourself if you experience that. This was one of the two outcomes, where the conversation continues. The process I’m about to lay out also works when you don’t know how they’ll react or when you’ve been pursuing your dream but you’re feeling guilty, frustrated, and like your family isn’t seeing as much of you as they should. This process is going to help you feel better about setting time aside for yourself to pursue your dream without feeling guilty, like you’re doing it at the expense of your family. It’s going to help your family get on board and be supportive of you.

Presenting Your Dream

• 25:13 Communication is obviously the most important thing, but I really like this framework. Schedule a meeting and think of it like you’re going to give a business presentation. Invite your spouse and your kids of a certain age, whoever is going to be affected the most by your decision to do this, and allow them to be a part of that meeting. Let them know, “I’ve got this dream, and I want to talk to you guys about it. I have some ideas, and I want to make sure that I tell you what I’m thinking so we can all be on the same page.” Step two is to come up with at least a rough version of a business plan to share with your family. What does pursuing your dream look like? What does achieving your dream look like? Describe that. Define the steps you’re going to need to take to get there. Talk about how long you think it will take.
• 26:11 Rachel: This is a really good thing to have for yourself anyway.
• 26:17 Ben: There are two benefits to this. One, it’s great communication for your family, because it paints a picture for them. Two, it’s great for you to get into the habit of not just looking at your dream and the idea of it but thinking about the details, the specific plan you have to get there. If your dream has some monetary aspect to it, and not all dreams do, bring that in as well. Say, “This is going to be an investment for this amount of time, and after this amount of time, I expect to start seeing some returns. This is what I think it might look like.” It’s fantastic for your kids, because you’re demonstrating to them what it looks like to have a solid plan in place for pursuing your dream.
• 27:22 You’re also giving your family the opportunity to bring their ideas and experience into the conversation. Maybe they’ll see something you weren’t able to see. This could get into some difficult territory, where they have an idea about how you should pursue your dream. Ben Flack said, “I’ve experienced strong reactions, not against pursuing design, but pursuing it through selectivity. Things like the One Concept approach, or the idea of saying no to people who want to pay me to do work. It can be perceived as harsh or egotistic. Ultimately, I can’t help how those who are closest to me choose to view those things, but how can I most helpfully communicate to address those concerns and give them the best shot at understanding it in a positive light?”
• 28:30 It’s good to address those concerns and to hash that out through conversation. Make sure you communicate to them that you understand where they’re coming from. Do your best to make a case for why your method makes more sense. If you end that and disagree, because it’s your dream, as long as they’re saying they’re going to be supportive of you, that really is your decision to make. It might be good, early in the conversation, to say, “I really want to hear your thoughts and ideas, but ultimately, I need to be the one who makes the decision about how I go about doing this. I value your thoughts and opinions.”

Agree on a plan for when and how often you’ll work toward your dream.

• 29:33 This is where you get into, specifically, what day of the week or what days of the week and how many hours of those days. How consistently? Is it going to be every week? Is it going to be every day? Is it going to be once a month? Define that and mark it out in your calendar so you and your family protect that time. Finally, schedule checkpoints and “boyband” meetings. You’re getting everybody on the same page again, reconvening. It’s the same purpose as the original meeting where you tell everyone what your dream is, but it’s an opportunity to reestablish that, zoom out, and make sure you’re still going in the right direction, and to get everybody “NSYNC.” If you’ve got a better title for that meeting, I’m open to suggestions.
• 31:04 You all want to be dancing to the same song. Checkpoints are there to track your progress. During the meeting, if you share some kind of plan, it’s a great idea to say, “Six weeks from now, this is what I want to have accomplished.” Schedule a meeting six weeks out so you can get back together and say, “This is what I did. This is what I accomplished. These are some of the mistakes I made, these are some of the surprises that happened.” Rehash that, and that becomes a form of accountability for you. It serves as a reconvening to make sure everybody’s still on the same page. Have that reconvening meeting less frequently, like once a quarter or twice a year. Everybody gets together, and you say, “Hey, I’m still working toward this. This is what it is. This is where I shifted my focus, so I need to bring that back in or change my activity to match the direction of my focus.”
• 32:24 Make sure that you schedule time intentionally to keep your family on the same page. In doing that, you’re going to ensure that you’re not going to get three months down the road, and suddenly everyone’s questioning, “Why is Dad still doing that?” You need to reignite those embers from time to time. Kelly Locket said it well: “You need to make sure everyone is headed in One Direction.”

Communication Is Key

• 33:34 Cory Miller asked, “Is it worth trying to get your extended family on board with your dreams when their dreams for you are completely different?” We’ve pretty much answered that question—no, do your own thing. Honor those relationships, glean what value you can from their experience and wisdom, but you’re the only one who can make the decision about how you’re going to pursue your dream. Simon asked, “How do you get your family on board when you’ve had a good paying job for the last 16 years but will have no stability in five years?” He went on to explain that the government department may be privatizing and merging, and it’s going to result in 50% job losses. His wife and his brother work there and are in $70,000 to $95,000 a year jobs, and they’re refusing to acknowledge the need for a Plan B in case their job goes away.
• 34:40 Rachel: I lost my job a year ago, and this was a really good thing. This job was shriveling me. We spent the three months before the ending day, which was January 31, coming up with a plan. Ironically, the last day was two days after we had our sixth baby boy. We didn’t know if our plan would work. I was really nervous about it. I think having a plan really helped me with that time. I tend to be a person who needs security and needs to know that we’re going to be taken care of. I got on anxiety pills at that time because I was dealing with so much anxiety about it all. Having a plan helped tremendously.
• 35:53 Ben: Rewinding to a period of time when we didn’t know what was going to happen and we didn’t know Rachel’s job was ending for sure, what if she had told me, “They’re merging conferences. Things are changing up, and there’s a possibility I’ll lose my job”? You’ve got to be persistent with that conversation, but be careful not to come across as the voice of doom, like everything is going to fall apart.
• 36:34 Rachel: You can do that at first. I did it at first.
• 36:47 Ben: Maybe Rachel doing it first was what helped me to legitimize it more in my own mind. There’s an underlying belief that there’s security in employment, and it’s very difficult to talk someone out of that belief, especially when they don’t realize the fault of that way of thinking. Another value you can assert and try to build into your family is to always have a plan, not because you’re afraid, but because you’re smart. You want to be ready.
• 37:38 Rachel: Plans can change. It doesn’t mean that whatever we’re putting as a plan has to remain set in stone. Plans can evolve. If you get to the end of the first month where nobody’s working and the plan you made is also not working, then you can reevaluate. That’s what we did for the entire year last year. We were constantly saying, “This isn’t working. What can we do now?” It’s a scary place to be, and we’re still in it a little bit. We’ve grown and learned so much, especially me. Ben’s always been the one to say, “We’re going to be okay.” I’m the one saying, “Do you realize we have six kids?”
• 38:38 Ben: Scott asked, “I find that my family says they’re on board, but when it comes to me executing the work, I feel like they’re not. I find myself being a bit of a broken record, trying to explain that for me to excel at my passion takes a lot of work. Should I just ignore it and keep pushing forward and hope they’ll see my progression, or is there something I can do earlier on that will help them understand why I work so hard?” This goes back to that meeting.

It is very important to establish expectations with your family.

• 39:14 If your family is surprised at how hard you’re working, it may be that you didn’t provide the expectation that you would be working that hard and that’s what it would take. There’s also the possibility that you did provide that expectation, and over time, it’s faded. That’s why reconvening and continuing to come together and get on the same page is really important. I don’t think you can be too persistent with that. If your dream is that important to you, it’s absolutely okay to continue to reeducate over and over again if you need to.