Are you all in?
Why we hold ourselves back (to protect what feels shaky)
Mindset Mastery is a weekly newsletter about the psychology of self-employment from Jenni Gritters. If you’d like to support my work, become a paid subscriber for $5/ month! Paid subscribers receive monthly business planning exercises (like the one attached to this newsletter!), along with access to newsletters on sensitive topics.
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Okay, on to today’s content:
Meet Jessie! Jessie wasn’t sure about freelancing. Maybe I should get a full-time job, she thought. Maybe this isn’t working for me.
Jessie wasn’t making as much money as she wanted to each month, and she felt like she couldn’t get from where she was currently at to her desired income level without suffering. She’d pitched a few new clients but when she didn’t hear back, she never followed up. Even though she’d been working for herself for a few years, it felt like momentum was slowing down. Soon, Jessie worried, she might be at a standstill.
When Jessie presented me with her situation, I offered some loving truth:
“Are you all in?” I asked.
Jessie looked up from the page where she was taking notes. “I don’t know what you mean,” she said.
I asked her the same question in a different way: “What would it look like to fully commit to freelancing?”
“Oh,” she thought about the question quietly. “I guess I’m not fully committed. I’m like, one foot in and one foot out because I haven’t ever fully DONE this.”
“Why not?”
Her answer came quickly: “Because I’m afraid.”
Jessie is all of us. She’s not alone. It’s a well-known phenomenon in psychology that we limit ourselves in order to stay safe. Here’s a good example: Have you ever gone into a testing environment and completely avoided studying? Most of us have had this happen at least once, and the reason behind it is quite rational: If we fail, we can just say, “I didn’t really try!” The blow is easier to take.
If you put all your effort into something and you fail, it can feel like you’ve put everything on the line. If you fail, everyone will know that you did your best and it didn’t work. In other words, the more we commit, the more risky it can feel.
I’ll ask you the same question I asked Jessie: What would it look like to fully commit to your business this fall?
Jessie answered this question with a description of a freelancer she was jealous of: This person marketed regularly by reaching out to new clients, and they had a system for following up. They charged a living wage, and had a system for managing their finances so they knew how much money was coming in and going on. They were able to take Fridays off. This person had freelance “coworkers,” or a community of folks who knew what it was like to freelance and could offer ideas. This person invested in regular certifications and learning opportunities. This also person worked in a steady way, and could talk clearly about what they were offering.
It was easy for Jessie to explain why this worked for someone else. And as she described this person out loud, she realized: If she wanted to fully commit, this was her to do list.
But we needed to figure out why she wasn’t doing all of this in the first place. When we dug into it, I learned that she had a very critical mother who wasn’t supportive of freelancing. Every time she started to step into her business fully, Jessie became buried in negative self-talk: This isn’t a valid career path, you aren’t smart enough to make this work, they’re not responding to you because they don’t like you, and you will never make this work.
Was this true? It felt true, Jessie said. And it was such an overwhelming thought pattern that it caused Jessie to freeze.
But, when we dug deeper, we found that she also had proof to the contrary: She’d been running a freelance business for several years, had worked on many incredible projects, and she’d even won an award for her content marketing work.
Jessie was also incredibly worried about what her parents would think if her business didn’t work. She was so terrified of telling them that her business felt shaky that she often didn’t talk to them at all. But, she kept telling me, freelancing worked for her because of the freedom. She didn’t really want to do something else.
Jessie and I decided to stage an experiment: Over the next three months, she’d go “all in” on her business. She’d put in the effort needed to level up, just to see what would happen. After those 3 months, if things still felt shaky in terms of her finances and clients, she’d apply to full-time jobs.
You can probably guess what happened: Jessie didn’t apply for full-time jobs. Her extra focus and effort to shore things up in her business made the entire operation look (and feel) more professional. As a result, Jessie’s confidence increased and she was better able to land client work. Consistency and hard work created an environment where Jessie could thrive. And she finally had proof of what she could really do if she went all-in. It wasn’t perfect, but it felt like a much better — and more committed — relationship that she could invest in.
(If you’re a paid subscriber, you have an exercise headed into your inbox right now that will help you figure out what “all in” looks like for you, too!)
I also want to say this: Sometimes we find ourselves in seasons of life when we can’t go all in on our businesses. This is completely valid. The “just do it!” mentality isn’t what I’m talking about here; we all know that’s BS bro-speak. Life is much more complex than that. So if you’re reading this and thinking, “I feel obligated to go all in, I feel guilty that I’m not all in, but my life circumstances make it impossible to go all in right now,” know this: If the time isn’t now, it’ll come. Stay where your feet are.
But if the time to go all in IS now, let this be your permission slip to step into the power I know you have. Put the effort in — really, truly, with focus — and see what happens. The results may surprise you.
Xo,
Jenni
Curious about my background? I’m a writer and business coach based in Central Oregon. I have two small children and I work part-time so I can spend a lot of time with them. Lately, I’ve been obsessed with non-linear business building and teaching people how to build successful businesses that support their human needs first. Check out my coaching offerings here, follow me on Twitter & Instagram, or download my free business plan for creatives!
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