2024 Lessons Learned As a Small Business Owner

Written By Jeannie Andresen
 
 

Happy 2025!

It’s a new year which means a clean slate, new goals, and that I’m walking into 2025 wiser than my 2024 self.

And that’s really the goal, right? To grow wiser.

It means you’re out there doing things, making mistakes, and learning from them, which allows you to be even better the next time you do the thing.

And that’s a lot better than… you know, being exactly the same.

Well I really feel that this year.

Because 2024 was… let’s just say, not my best year.

There were quite a few things that were hard for me in 2024 that really forced me to pause, ask questions, learn, and grow.

And because it’s important to me as your business guide to take you along my journey, too, I’ve decided to go public about my lows from 2024. Because not enough people talk about them.

So without further ado, here is my complete breakdown (a fitting word) of 2024.

The hard, the wins, and the lessons I'm walking into 2025 with.

Let’s dive in.

What Was Hard in 2024

I suddenly had a lot time… for sad reasons

When I say 2024 was not my best year, just know that 2023 was my absolute worst year ever (with a couple good moments).

My mom was battling terminal cancer, I was planning a wedding and praying she would make it, I spent at least half of my waking hours traveling to/from the hospital, being in the hospital, or being at her home by her side.

When I learned she wasn’t going to make it, we had an impromptu wedding in her living room.

After she passed away, I was grieving losing my best friend and north star, yet still having a wedding to plan (in Greece, of all places).

Then our dog Rebel tore his ACL and we were 5K out + on lockdown, caring for him right up until we were leaving for our wedding.

(Side note, if anyone ever has to go through a dog ACL surgery recovery, this product is a lifesaver.)

We had the wedding of our dreams and spent the month of September in Greece.

Then I came back and was hit with all the grief I didn’t have time to process, and needing to build momentum again in my business.

So 2024 began with me staring at my empty-ish calendar and feeling so many mixed emotions on how much time I had to give to my business (a lot) and the reason why I had so much time (because I was no longer caring for my mom).

It was hard.

Our dog was really sick

In February, Rebel fell extremely ill with a sickness that took six months, three different vets, countless vet visits, and 10K+ in vet bills to finally diagnose.

During that time every 2 days he would stop eating and then start a 48-hour cycle of non-stop vomiting, much of the time in the middle of the night.

We weren’t sleeping and our anxiety was sky high. My focus was shit.

After months of trying everything, he was finally diagnosed with inflammatory bowel disease.

We then found a food + medicine formula to keep it under control.

So thankful to be here now, but that was a really hard time in life (envision me in the middle of a coaching session while simultaneously hearing and seeing my dog vomit off the couch, onto the rug, just five feet away. It was hard.)

Our condo wasn’t selling

In May we put our River North condo on the market fully expecting for offers to come pouring in, only to receive crickets.

Well a big learning here is to pay attention to the market, because I did not know that I bought that condo in a sellers market and was selling in a buyers market.

We chose to move regardless because we knew it was best for us, and we knew the condo would sell eventually.

It did, and we finally closed this past December. But financially, things were tight for a while (2 mortgages + Rebels bills… ugh). Plus I lost a lot of money on the condo and sold for less than I bought it for.

I didn’t have my mom

Navigating the first full calendar year without my mom was more than hard.

Everything is different, in ways I feared and in ways I could never have imagined.

It just sucks and it’s lonely, despite my wonderful husband, all the amazing people in my life, and having a great therapist. There’s just nothing that replaces your mom. Especially mine. She was legendary.

Business School wasn’t flying off the shelves

Something was going on with my business coaching program Business School for Designers. What was life changing for my first handful of clients was now challenging to market and draw interest in.

I eventually hired a business coach (more on that below) and decided to put a pause on selling it further.

2024 Wins

Moving! Definitely.

Despite our condo not selling, we made the decision to move.

We found the perfect little home to rent in Highland Park (literally the first time since college that I’m renting - I was a 2x homeowner in my 20’s!!!) and we knew we needed to take it.

It’s honestly been the best decision we could have made.

We’re walking distance to so much and my best friend is just a mile away (the closest we’ve ever lived to one another - it’s awesome.)

It’s *very* weird not being a homeowner but ego aside, it's sooooooo nice. No HOA fees, no fears of leaky roofs or an appliance breaking, etc.

ICYW why we chose to rent (my mom definitely is) here were our main reasons:

  1. Jacob wasn’t committed to the Chicago area. He isn’t from here and was unfamiliar with the ‘burbs. Prior to moving to HP, he wasn’t sold on living in Illinois long-term. He really didn’t love Chicago and was 100% not about to put a down payment on a house to live here permanently. Good news! Now he’s obsessed with Highland Park, the N. burbs in general, and is ready to run for City Council (kidding - but not really).

  2. The suburb market is just bananas right now. Nothing is on the market, and whatever is is going for way over asking price. We just did not want to play that game and spend insane money on a house we weren’t excited about that would eventually dip in value. But again, even if it were a great market, we probably would not have bought due to reason #1.

All that to say moving was 100% the right move for us. We are where we were meant to be.

Being ASID Chicago’s Keynote Speaker

I was selected as ASID’s keynote speaker for their Business Bootcamp in May of this year, and it was such an honor! I spoke on “how to achieve balance in your design business” and absolutely loved the opportunity to help more designers at a higher level.

Shameless plug - if there is *anyone* I should be connected with for speaking at design events this year, please let me know!

Hiring a Business Coach

It was apparent halfway through the year that I was not serving designers nearly at the level in which I desired to. I knew I needed some guidance on my programs so I could have programs that offered a ton of value to the industry.

I decided, despite “not having the money”* (see note below) to make a five-figure investment and hire a 1:1 business coach who has built multi million dollar service-based businesses.

This money was the best money I have spent in my business thus far. She helped me work through my programs, decide what to keep and what to ditch, and helped me refine my messaging so my ideal clients can recognize that my programs are for them.

And yes - Client Success Academy was born from her seeing the material I had for this program (formerly my 1:1 VIP Days) and her saying that THIS is what the design community needs from me.

I was ecstatic because this + private coaching was what I enjoyed marketing the most in my business.

*Note when people say this, it is rarely ever true - I could have made this excuse with all of the above happening, but knew this was best for my business. I couldn’t afford NOT to do this.

Client Success Academy

Even just seeing these words, I could cry.

It’s the most perfect title for a program that truly brings client, designer, and business success.

This is Client Success Academy’s first week of my January program and while I know there is still going to be a lot to learn (did anyone catch my stories from Monday on the two tech glitches that happened on day 1????) I just know that this program is going to do amazing things for all the designers who participate in it and the clients who work with them.

Working with Solo + Small Team Designers

Upon auditing my client base I realized that my private clients are…

  • Women

  • Solo or small team (3 staff members or less) designers

  • About 90% are moms

Also, close to 75% of these private clients re-enroll in working with me after our first program together.

The value I’m able to provide these individuals is unmatched.

They get…

  • someone to vent to that isn’t their husbands

  • someone to set goals with and hold them accountable

  • solution-based guidance on their biggest challenges (vs a complain session with their peers)

  • someone who will single handedly create a personalized script or email template for any client challenge they are presented with

  • someone who has hired, trained, fired, and managed so many employees in their career

…all allowing them to be better designers, business owners, and leaders.

I have helped MULTIPLE clients of mine prepare for maternity leaves, too.

I am realizing this is a core need in the industry and something I plant to create a tailored program around this year.

I have amazing relationships with my private coaching clients and am so thankful for them.

This was definitely a win.

Supporting Large Teams Differently

That said, this year I had some amazing opportunities with larger teams.

One female-led commercial design firm struggled with establishing authority with their clients, having their clients follow their processes, and were losing a lot of money because of it.

I altered my VIP day to meet their needs of their larger firm and we worked together to create a client process that solved for this. We’re now working together quarterly for leadership coaching.

Additionally, another principal residential designer with a large team noticed that I could maybe help them with their client pain points.

I pulled all their materials, studied their processes, gathered what their greatest struggles were, and created personalized scripts, email templates, and tips for how to enforce boundaries, part ways with clients who aren’t making progress, fire clients who are toxic, you name it.

It was so fun to put together and the team was a delight to work with.

What I’m Doing Differently In 2025

When I was 24 I worked with my first ever coach, and I remember her pinpointing that I take a “Ready? Fire. Aim.” approach to my work.

I could not have felt more seen when she called this out.

I mean, I used to purchase furniture without measuring (I know you’re cringing!!), I launched a business without a plan, I even create same-day Instagram posts out of urgency and not out of alignment.

And while taking action is always better than not taking action at all, the results can be so much sweeter with aligned action.

With aiming.

So to walk into 2025 with CSA, with more clarity than ever on my ideal client, after learning from such an established and prestigious coach, this all has really led me to a place of being able to aim before firing.

And that’s what I’m really bringing with me into this new year.

Will report back on how that goes, but you’ll have to wait a year. So hang with me.

XO

Jeannie

Psst - want to reflect on your year last year and have a better plan for this one? Download my FREE Business Breakthrough Workbook and declare that this year will be different than last.

My Favorites List of 2024

Favorite Books of 2024

Favorite Recipes of 2024

Favorite show of 2024

  • Nobody Wants This, hands down. If you haven’t seen it, it’s a cross between My Big Fat Greek Wedding and Crash Landing On You (IYKYK). It’s a masterpiece and the moment it ended, I missed it. Can't wait for season 2!

Favorite movie of 2024

  • The Merry Gentleman. JK - I honestly can’t even recall one movie right now but if anything comes to mind I’ll circle back. Is there a Goodreads for movies? Is that IMDB?

Jeannie Andresen
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