I’ve been told my decisiveness is one of my best qualities as an entrepreneur.

But the decision to sell my company, Workweek Lunch, was nothing but one-and-done. Instead, it was a culmination of unpredictable moments and slow, painful realizations about my work and how I really felt about it. It was unlike any decision I’ve ever made and led me to confront the biggest challenges of my life.

The time between first exploring various paths away from my company to actually leaving it was exactly one year.

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My first big mistake: taking a valuation as a challenge

The possibility of selling Workweek Lunch first crossed my mind In 2021, after completing The Workweek Lunch Cookbook.

Inspired by a post in a Facebook group from a well-known food blogger talking about how she sold her blog through a broker, I couldn’t help but think, “I could do that too!”

At that time, I experienced significant burnout and a growing desire to move on from Workweek Lunch. As someone who follows numerous entrepreneurs online, I knew selling a company was a huge accomplishment. The idea of handing everything over and walking away with a bunch of cash sounded appealing. The only reason I hesitated was that my business was thriving! Curiosity got the best of me and I reached out to the broker she recommended.

On that call, I discovered that selling my company was possible. The broker even gave me an unofficial valuation, which I saw as a personal challenge. Determined to prove myself, I set my sights on doubling that valuation.

Lesson learned: Quit while you’re ahead.

Looking back, I wish I could shake some sense into 2021 Talia.

I didn’t know it at the time, but the unofficial valuation was so good! At that point, business was going well, with steady growth and success. In hindsight, that was the ideal moment to seriously consider selling. I realized when things are going great and burnout is just starting to make an appearance, that’s when to start thinking about how to make a graceful exit.

Unexpected Roadblocks: Algorithms, Burnout and Disconnect

A couple months after my call with the broker, we noticed a major shift in Instagram’s algorithm in the wake of TikTok’s growing popularity.

This shift completely tanked our reach to new people and potential customers. Going from creating photograph-based content to video content was a huge lift for me and I was slow to pick it up. Even after two years of creating food video content, I can’t say I ever found my groove with a sustainable format and formula I liked.

These two factors combined (the algorithm and my resistance to vertical video) decreased our reach and sales slowed. On top of that, I went through a major breakup and moved to my own apartment in Seattle. I also didn’t anticipate how burnt out I’d feel after completing my cookbook manuscript.

Yet I pushed on for another year, chasing that goal of doubling the valuation.

Lesson learned: burnout isn’t to be ignored.

Breaking Point: The Decision To Move On

Right after a team offsite in NYC in May 2022, I reached my breaking point.

I felt completely disconnected and lost my drive for creating food content. The work that used to get me pumped up now felt like a chore. It wasn’t just a case of lacking inspiration; it was a clear sign that I needed to move on to something new. My burnout wasn’t just affecting me, but it was also holding my team back from making progress on projects.

I felt defeated and trapped, making it impossible to kick-start our growth again. So, I drafted up a 12-month plan to shut down Workweek Lunch.

At the time, I didn’t see selling as a possibility. Who would want my company if I didn’t want to be a part of it anymore, or if it wasn’t growing?

As a business owner, you can’t just quit when you feel it’s time to move on, especially if your business is based on a subscription model. I longed for the luxury of putting in two weeks’ notice and shutting it down felt like the best option.

Letting My Advisors Talk Me Off The Ledge

After consulting with my close friends and family, they urged me to talk to other entrepreneurs. And you know what? They were absolutely right. Taking their words to heart, I tapped into my trusted network to gather some valuable insights. So, here’s the scoop on the priceless advice I received:

• Take a vacation – a real one – for over a week.
• Delegate more of the tasks that drain you.
• Figure out what lights you up in your business.
• Explore different options for exiting while maintaining ownership.
• What I’ve built is amazing and hard to repeat.
• If I want to start a family soon, it’s better to have a stable income vs starting over.
• There are always going to be parts of the business you don’t like.
• Find a community for entrepreneurs with shared experiences.

I had a lot to think about. It seemed like everyone I spoke with pushed me to stick with it and find a way to stay. The consensus was that I was just burnt out and needed to change some things in my biz.

Lesson learned: when you hit a tough spot, reach out to your community. I wish I had talked to them before mapping out how I’d shut it all down.

Recommitting: A Last-Ditch Effort To Make It Work

I took their advice to heart and made a point to take real time off. Picture this: a blissful 9-day solo getaway in Hawaii, completely unplugged from the digital world. It was my first real vacation in six years and exactly what I needed to recharge.

When I returned, I delegated more responsibilities to my team, lightening my workload so I could rediscover my passions inside and outside of my company. I reduced my working hours and recommitted myself to Workweek Lunch.

Unfortunately, that phase only lasted about 3 months.

It hit me like a ton of bricks. In October, I found myself sobbing to my stepdad on the phone about how unhappy I was, telling him about my shut-down plan. The depression had become unbearable.

To me, leaving behind what I had built was a failure. I couldn’t help but compare myself to other food bloggers.

Why were they content with doing this for over a decade while I struggled to make it beyond six years? Why couldn’t I be the type of person who could sit down and get the work done even if it wasn’t fun for me? Why did I constantly crave excitement in my work? These questions gnawed at me.

I turned to my friends and asked them how they managed to stay motivated and engaged in their jobs.

It was fascinating to see that each of them had discovered a sense of purpose, even if it was as simple as “My job supports the things I love in life.” While I knew the products and services my company offered were positively impacting many lives, that alone no longer provided the driving force I needed to show up and do the work.

Lesson learned: I’m not a robot and it’s okay to want work that excites me. I am privileged to be able to choose work that’s fun.

Finally Deciding To Sell

When I reached out to my boyfriend to share my overwhelming desire to quit, it was at that moment I ultimately decided to sell. Although he hadn’t been with me from the very beginning of this journey (we had only been dating for four months), he had a deep understanding of my entire experience. He encouraged me to consider selling instead of shutting everything down.

Together, we crunched the numbers, and he was right—selling would put me in a better financial position, even if it didn’t come close to the estimated valuation from 2021. Doubling it was out of the question now. Nevertheless, I knew I had to make moves.

I have a personal rule to always take the bigger risk. My mantra for 2022 was “take more swings” and this was my biggest swing yet. I was ready.

By the end of November 2022, I was lined up with a broker, a legit valuation, and a plan to put the company up for sale in January 2023.

I’ll talk more about the process from there in another post! Sign up for my monthly newsletter to get the updates right in your inbox.

The takeaway:

I’m not sure when this idea implanted itself in my brain, but I’ve always heard that business decisions aren’t supposed to be emotional. Historically for me, they haven’t been too emotional until now.

As I reflect on my journey of deciding to sell my company, I see that idea, while practical, isn’t my reality. This decision was a rollercoaster ride of anxiety, depression, burnout, doubts, and tons of risk. Yet, through it all, I discovered the strength to embrace change and get out of my comfort zone.

I knew what I wanted all along, but coming to terms with wanting to walk away was the challenging part.

Deciding to sell Workweek Lunch wasn’t a sign of failure. I’m not a quitter for doing it. It was a bold and necessary step toward my personal and professional growth. Along the way, I encountered valuable advice and learned so many important lessons that I can’t wait to apply to my next endeavor.

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