Tips on Getting Through Your First Year of Entrepreneurship

Where has the time gone?

I’ve asked myself that question many times this year. When I received the invitation for my 20-year high school class reunion. When my older brother, who I never thought would actually become an adult, had his first child. And just yesterday when my company Brian Thompson Financial turned a year old!

The words “my company” still shock me.  I never thought I could do something like this. I’m super risk averse and like to have a detailed plan of action when making a decision. That’s a pretty debilitating mindset for a person that must deal with a vast amount of unknowns when starting a business.

But I did it, and I made it through that tumultuous first year!

I gave some tips for budding entrepreneurs when I first launched. Much of that advice still applies, especially the part about getting comfortable making mistakes. After this first year, I’ve realized a few more things that I didn’t foresee back then.

So I wanted to provide a few more insights today to help any of you thinking about taking the leap.


You need support

Starting a business is hard

This seems pretty obvious, right? I heard it many times before and after I launched. People warned me especially about the first year.

“It’s going to be stressful.”

“You’ll doubt yourself many times”

“Some days will just suck.”

I believed what people told me. I never thought it would be easy. But I still couldn’t comprehend how hard it would be. In the back of my mind, I still thought, “it probably won’t be that bad.”  Turns out, there’s a huge difference between acknowledging something and experiencing it.

Just keeping the business going was stressful. I didn’t know whether I could attract and retain clients. I agonized over whether I was choosing “the right” processes for the business. I pored over my financials constantly to determine how long my savings would last.

I’ve had a few experiences with this kind of stress in law school and even starting the blog four years ago while still practicing law. But launching the business took stress and anxiety to a whole new level.

Luckily, I have a supportive husband.  Ben worried about me when I wasn’t sleeping and wouldn’t get too upset with me when I was super irritable. As sweet and genuine as his support was, though, I never felt like he really understood my stress.  To fully release that anxiety, I had two amazing mentors, two study groups (a group of similarly situated entrepreneurs) and a therapist who could really empathize with my situation.

You will need a support system to help you through these times. I can already see some of you saying “it won’t be that bad.” Just remember these words when you get to a point where the stress really weighs on you.


It’s your business. Make it what you want.

I also underestimated the amount of joy creating my own schedule provides. I really, really like being able to go to the gym in the middle of the day when it’s almost empty. I love working at night when Ben or friends want to hang out during the day. And I love not having to ask for permission to take off for the afternoon.  I never really understood the satisfaction that brings, and I’m relishing it now.

That being said, I also found at times that flexibility was a hindrance. Especially early on, I worked into the early morning after Ben had gone to bed. People told me that I shouldn’t do that because I would burn out quickly. So I tried to cut back on the hours, but that only led to sleepless nights because I didn’t feel like I was getting enough done.

My therapist convinced me that I needed to do what worked for me. If working late at night reduced my stress and allowed me to sleep, I should do that. I could compensate by starting later or taking a mid-day break. In the end, I had the ability to create what I wanted; I just needed to figure out what that actually was.

Creating what you want also includes choosing who you want to work with. I’ve been lucky to have found some amazing clients and got on the niche bandwagon from the beginning.  But that decision to say “no” to the tech-phobic retiree was still difficult.  And when I didn’t say no, he ended up weeding himself out. One of my mentors reminded me that you can’t just focus on the short-term (even though that’s important). Eventually the 1st year will go by. Then year three. Then 10. You want to think about where you want to be at those points too.


Reflect along the way

As I said, time flies. And none of us know when our time is up. I found myself moving quickly to the next thing without taking time to reflect and celebrate along the way. Ben and others helped remind me to celebrate the milestones. Getting the first client. Reaching a point where the business started to pay for itself.  I even began to enjoy the adrenaline right before a client appointment. I looked forward to a text from Ben saying he’s proud of me.

I’ve started keeping a journal to help with reflection, but you can use whatever method of helps you process what you’re experiencing the best. I’ve become even more grateful for the clients that believe in me, my husband who supports me and all of the other people who have helped keep me going. These points of reflection have also made getting through the tough times a bit easier.


Speaking of reflection, I want to end by saying thank you. I don’t know how to phrase it without sounding cliché, but I couldn’t have done this without you all. Thanks for the support and encouragement. Thanks for the referrals, shares, likes, comments. I hope to pay your kindness forward in the years of good service to come.