A Letter For The Hard Days
Going back into insurance is a big deal for me. I know I've shared this story previously, but it has been a while, and there are a lot of new readers on the blog, so I'm going to give the quick version. When I graduated high school, I dreamed of going big in my parents' insurance company. I worked part-time throughout college, making decent money, and planned to go full-time when I graduated, which I did. That didn't work out as well, though. At the same time I graduated, my boyfriend (now husband) returned to Florida for training when the base finally reopened after Hurricane Michael.
I started off working strong but quickly realized I would much rather be with my boyfriend. Add to that the fact that I had moved a couple of times in just a few months, and life became very chaotic. Anything that kept me in North Carolina rather than taking me to Florida became the enemy. I stopped working as hard or consistently in insurance, which tanked my success and burned me out. When we got engaged, I took a step back to figure out exactly what I wanted to do because insurance just didn't feel right anymore.
That's when I found my new dream of writing a book, and that dream grew to include supporting military spouses as I met so many who had had their dreams stolen within military life. I walked away from insurance. I always knew that one day, I would go back in some capacity, and I never cut ties. I still attended every conference and started running some programs out of my parent's office to help them. Back in September of 2023, though, I got the sign that it was time to get back in the field.
Here's the thing, though. I left insurance in a really negative place. I never blamed the company, people, or system. I took full responsibility for my failings within it and never harbored negative feelings about the industry. But because of the state that I left it in, I had a pit in my stomach for the longest time whenever I thought about returning. When I got that sign back in September, for the first time, I didn't feel that pit, but I also knew it would come back.
This isn't a perfect job, and I am not a natural at it. I'm still going to go through a learning curve. I will still have the same bad days I was having back when I was successful because bad days don't go away even if we're doing the right thing. I will figure it out through a lot of trial and error, but while I go through the error, I feel pretty confident that the pit in my stomach will return. And I need to be prepared to fight that feeling because back in September, there wasn't a shadow of a doubt that this was anything other than the right time. So I've written myself a letter for when the bad days come because they will, but I also can't argue with the clarity I received. The only thing that will get me to back out now will have to be that same level of clarity, and I'm betting it will come when my dream is ready to go full-time.
Dear Sarah,
I'm writing this a few months after the fact, but I remember how it felt and know how you're starting to feel now. In September, you went to Breakthrough. You have been wanting to make a difference in Mama and Daddy's business. The biggest way to make that difference is to show other people this opportunity, especially when you meet so many people who would be natural at it. But you quit, so how can you tell anyone else the greatness when you quit? You needed to rectify the story. That's where you were at when you heard a speaker talk about the buyback loop.
That speaker talked about delegating before you hit the pain point. You didn't do that all those years ago, and it burned you out. That was a big realization. You left the conference knowing that you needed to reframe the story. This wouldn't necessarily require getting back in the field, but it would require removing the blame from yourself. It was immaturity. You weren't ready. You put immense pressure on yourself. We are allowed to forgive our younger selves for the mistakes they made because they did the best they could at the time. You have a new dream now.
So, you boarded the plane home, prepared to rewrite the story. When you landed in Dallas, you had a voicemail from your favorite clients. That was undoubtedly one of the more unmistakable signs you've gotten. That was when you realized you needed to get back in the field. This time, there would be no pressure. This time, we weren't trying to get promoted and rise within the ranks. This time it would be fun. You'd make extra money to do the things you dream about and maybe win the trip.
You felt peace in that moment. You felt peace about the decision. The pit in your stomach about going into the field had disappeared. It was a bad time to get started, though. It was an excuse, and life was chaotic, so February was the beginning.
There are debts to be paid. There are vacations to go on. There is fun to be had with the money you make. That pit is going to come back. It already has a bit, but this time, it's there to hold you back, not keep you on a different track.
At that moment, on the plane in Dallas, it felt too right to be wrong. It was so clear. I don't care if you kill it. I care if you quit. It's been almost five years since you took your break. You have grown. You are stronger. You are more mature. You have it in you to kick ass exactly the way only you can because your dreams deserve it.
The military dream is still intense, but you need money to support it and supercharge your growth. The time is right. Set the pace and run your race. When the pit comes back, remember why you started in the first place. Borrow her faith in October and mine in January because I believe in you.
Love,
Sarah
I write letters to myself a lot. Whenever I feel particularly strong about something, I write a letter because I know there will be days when I'm filled with doubts. On those days, I can turn back to the faith I had a few days, weeks, months, or years ago to maintain my faith when things get hard. It helps keep me on track and get through the bad days. I know the hard days are coming, but I also know how clearly I got the answer I needed. I won't let go of that until the time is right, which certainly won't be on a bad day. I'm only going to quit when the good days don't feel right anymore, and it's time to shift focus. Sarah, five years ago, would have thought I was brave for doing this. Sarah, five months ago, knows I'd be stupid not to. Trust yourself because only you know what's right for you. And you can always borrow the faith to get through today from the stronger version of you that got through yesterday.