Ready to Hop On Your Confidence Carnival?

Carnival Photo

Who am I? Am I too old? How good am I, really? These were the questions of a smaller, sixty-ish year-old man walking into Milwaukee Founder/Fest.

This may sound like a joke, “A man walks into a bar…” but it was my reality on February 15. Coincidentally, just days before I delved into the ebb and flow of confidence in a blog. That Thursday, the relentless battle between “You’re Great/You Suck” consumed me. Getting home at 8:45 pm, I realized I had spent the day on a series of chaotic carnival rides.

What Happened to Confidence on Thursday?

Excited for a packed day, my calendar brimmed with six diverse meetings – a mix of new connections and old friends. Balancing business development and client work, the day promised fun and challenges. I expected some regular confidence ups and downs. You know, the roller coaster. After this day, I realized life as a business leader is more like Six Flags – a lot of different rides. Hang on, let’s go!

8:00 a.m.     The Art and Science of Personal Branding Webinar                    Ride: Roller Coaster

Having a LinkedIn profile that reflects your unique personality is important. Mine needed an update, so I signed up. I initially hesitated because it was hosted by Women in Technology. Could, should, an older guy go? A friend encouraged me, and I figured having a name like Lynn I could sneak in, right? As the host welcomed women for coming, thanked women sponsors, and offered how few women are in tech, I felt out of place. My inner voice yelled, “You don’t belong!”

The session proved valuable and offered insights into questions we needed to ask ourselves, pitch strategies, and hints to perfect our profiles. I must admit that I gained marketing confidence but refrained from reaching out to others as I typically would.

9:00 a.m.     Client Time                                                                                                  Ride: Ferris Wheel

A very productive couple of hours. One client sought a confidence boost in accounting, so I revamped her income statement, created account groupings, improved Cost of Goods Sold reporting, and made up a cheat sheet to improve her accounting consistency. In the final hour, I reviewed another client’s Income Statement and fired off some tax prep questions. In the zone with confidence high, I could ride this all day!

12:30 p.m.     Podcast Exploration                                                                                 Ride: Flying Swings

My 2024 goal is to guest on 12 podcasts and secure my first speaking engagement. This meeting, with someone who could help, was fun. Sharing my podcast experiences, I discovered one host was her client. Small world! Prepared to discuss potential speaking topics, I offered:

·         Why Every Business Needs a CFO

·         Let’s Make Your Accounting Make Sense

·         You Don’t Know Your Customers as Well as Amazon Knows You!

I was confident that I had expertise and value to share. A smooth ride.

1:00 p.m.     Prospect Meeting Zoom                                                                            Ride: Haunted House

Time to pursue new business! My VA found a company looking for a Fractional CFO to work with their clients. While it felt like a job interview, we aligned perfectly in client offerings and value creation. I knew I did not have extensive construction experience, but did highlight how I helped a large home builder answer two fundamental questions:

·         Why were Profits not going up as fast as Sales?

·         Why do we keep missing our Cash Flow Forecast?

In many first-time situations, we wonder what is around the corner waiting for us. The ghoul with the axe in his head did not bother me!

3:00 p.m.     Personal Reconnect Zoom                                                                       Ride: The Scrambler

 Excited to reconnect with a business coach I met years ago, our conversation was unexpected. He wanted to talk about DATA! He has taken several data analytics courses and proudly admitted, “Lynn, I never understood it when you talked about the value hidden in data, but I completely get it now!”  He now has tools to help his clients even more than other coaches. He was on fire, and our fast-paced conversation reminded me of my journey from data guy to Data Magician to Fractional CFO.

 4:00 p.m.     Fractional United New Member Zoom Meeting                                         Ride: Bumper Cars

Fractional United, a new community tailored for professionals like me, gathered individuals from all functions a business needs. I would guess 60-70% were new to the fractional world. I offered my perspective after five years. “For those of you just starting, give me a call about the roller coaster career you’re signing up for!”  I was an expert in the room and can bump with the best of them!

6:00 p.m.     Founder/Fest                                                                                                         Ride:  Tilt-A-Whirl

 I attended Founder/Fest VI, celebrating Milwaukee's thriving founder community. As a successful founder, I recognized the familiar profile: passionate about their business yet lacking in financial expertise. Stepping into the event, I felt out of place in a crowd where everyone seemed young, tall, and stylishly dressed. Not me at all! The voice in my head screamed, "Fraud!"

A young lady checked me in and said the program started at 7:00 downstairs, but upstairs, there would be a bar, pizza, and networking (and I swear I heard her also say dancing) all evening. “Have fun!” I ventured upstairs and found comfort with a group of older men. Regaining my wits with small talk, I was ready to meet others. Over the next few hours, I had some great conversations and some that fell flat. I would not say that I overcame my self-limiting beliefs.

The evening felt like an in-person social media stream. I saw everyone living a much better life than me. This ride went up and down and jerked me around. But would I get on again? You bet!

The Confidence of Experience

I wanted to give new entrepreneurs a snippet of what you signed up for. As all experienced leaders will agree, you will have to put yourself into uncomfortable situations, do work you do not enjoy, and struggle to find more work as you do the work you find. You will mess up, get up, and do it again.

Confidence is something we all struggle with. I mentioned self-limiting beliefs that are in your head and mirror. New can be scary.

In an earlier blog, I noted that leaders face unique confidence challenges and that getting more information can help to overcome some confidence struggles. But nothing beats experience. Get out of your comfort zone, experience, fail, experience, succeed. Repeat. Over and over.

Take a different ride. You may come to love the thrill of roller coasters. If you need a partner, I will ride with you!