The Rollercoaster That Is Entrepreneurship

Read time: 8 minutes

Welcome to The Ascend Archives Tuesday Tale, a weekly newsletter where I share a story about a transformation, revelation, or change in thinking that has helped improve an aspect of my life.

Saturday at 7:34 PM:

“Think I’m gonna hold off on our product launch for a while… had another meeting with my old boss today and going to just lock back in with them.”

My heart sank into my stomach. I sat at the desk in my bedroom and read the text from my client again. Was this really happening?

This product launch had been in the works for 3 months and was supposed to go live in October. Of all my current projects, this was the one I was most excited about. The project I thought would impact hundreds of people. The project that would be the perfect case study for future work. The project that had the most potential to scale my income.

The negative thoughts started to flow…

Another client is gone, what if they all disappear?

I spent so much time on this guy. All for nothing.

I just told everyone how well things are going with my business. Now what?

15 minutes passed. From the outside, it was 15 minutes of silence. But on the inside, it was 15 minutes of chaos - running scenarios through my head, battling the negative thoughts, and figuring out what to do next.

I decided to text him back.

“Oh ok. Can you hop on the phone tomorrow or Monday to update me on what you’re thinking?”

“Let’s talk Monday”.

I put my phone down and turned on Do Not Disturb. At least he was still willing to talk with me. Let me learn more about what he’s going through. Maybe there’s a different way I can help him and salvage this situation.

I grabbed my Kindle and read a few chapters of Only the Dead, the 6th book in the Navy SEAL thriller that has had me hooked for the past 6 months, before drifting off to sleep.

—

Sunday at 5 AM:

After a solid 9 hours of sleep, I was wide awake.

There was nothing I could do about my client so figured I might as well have a productive day. I wrote a few pages in my journal, did a 10 minute Headspace meditation, read a few newsletters, and did some mobility exercises. Then, I headed to my home office to knock out my weekend newsletter.

By 8 AM, I was on the trail for a short 3 mile run before loading up on groceries at Trader Joe’s for the week.

By 12 PM, I had meal prepped shredded chicken, vegetables, pasta, and meat sauce for the week. I was crushing it, but I still had the entire rest of the day.

There was nothing left to do and the jetlag from Africa was catching up to me. So I spent the afternoon on the sofa watching football and catching up on much needed rest.

Around dinner time, a text came in from my client, “You good to talk at 5 PM tomorrow?”

I confirm the time and settle down for another early night to bed.

—-

Monday morning:

I was pumped to be back in Austin. Traveling, having friends visit, and going out on the weekend were all fun but I was itching for my routine.

On Monday I finally got to execute it:

• 5 - 6: Miracle Morning

• 6 - 7: LinkedIn Posts for an existing client

• 7 - 8: Proposal for a new client

• 8 - 11: Breakfast, run, smoothie, podcast, shower

• 11 - 2: Writing & Creative Work

• 2 - 3: Lunch break and walk

• 3 - 3:30: Haircut

• 3:30 - 4:30: Admin and email

Once 4:30 hit, I started thinking about the call with my client.

There was nothing for me to prepare. I had to just be myself, see where his head was at and find a way to help if I could. I didn’t want to force the guy to build something he didn’t want to build.

—

It’s 5:02 and I haven’t heard from him.

5:05… I try calling him, no answer.

I continue walking around the same small loop in my neighborhood staring at my phone.

5:10…nothing.

5:15…nothing.

Finally at 5:20 the phone rings.

I answer, “What’s up man! How are you?”

“Drew! What’s new my man!”

After some friendly small talk, I ask, “So how you feeling about this product launch, what’s on your mind?”

“I’m struggling with the uncertainty of this entrepreneurship stuff. I’m not good with systems and knowing what to focus on each day. It stresses me out. I want to grow my own brand and not work for someone else but it’s tough. My old boss offered to increase my pay if I fully commit to being a brand ambassador for them. I think it’s the right move for me right now. Are you a full time entrepreneur and do you struggle with these issues?”

“Yeah, I’m a full time entrepreneur and know exactly how you feel. It’s stressful dealing with the ups and downs and having to figure it all out on my own. But when I think back to the stuff I dealt with in my corporate job, I much rather be dealing with this stress and have the autonomy I have, than deal with the other obligations and shit that came with my old life…What scares you the most about pursuing your own brand and this product launch?”

“Adding more to my plate when I’m already struggling to keep up”.

“I get that and I don’t want to add more to your plate. But you’ve also told me in the past that engaging with people and helping them brings you energy and joy. This product launch will allow you to do that, but will your old job do that?”

“Not really.”

“Well I’m not tryna force you into anything but with this product launch, I’m setting up all the backend stuff. All you would need to do is just need to show up a few times a week to share your ideas, coach people, and answer questions. What’s the worst that can happen if we give this a try together?”

“That’s it? You’ll handle all the admin stuff?”

“Yep! We can just test it out and if it gets too much then we can shut it down.”

“I’m in. Let’s give it a shot.”

—

I left the call feeling cautiously optimistic.

We have worked together for 3 months, built a good rapport and have a baseline level of trust. He’s just overwhelmed. If I can simplify things for him and show him a proof of concept then maybe he will understand it’s possible for him to do the stuff he enjoys.

Immediately after the call, I wrote an email with next steps and action items on 10 things I’d do this upcoming week and 3 things I needed him to do.

I was determined to make this happen.

—

Tuesday morning:

• 5 - 6: Miracle morning

• 6 - 7: I knock out 2/10 of my action items for him

• 7 - 9: Play pick-up basketball

• 9 - 9:30: Smoothie and head to coffee shop

Another great start to the day.

When I got to Merit Coffee, I ordered my Black Iced Tea, and sat at a table outside. I was excited to knock out some writing and more items on my to-do list.

Just before I turned my phone on Do Not Disturb, I saw a text from my client:

“Think I’m still gonna hold off on things… just go all in on with my old company for now.”

I shake my head. I should’ve known.

—

Final thoughts

This is still very fresh as it happened yesterday. Things will change but I felt like documenting this in real time.

While I was frustrated and anxious about this situation in the moment, I’ve been able to take a step back and reflect. Here’s where I’m at:

1. Working with the right people: My client clearly has a lot going on and this product launch is not his top priority. Yes, I see tons of potential with this opportunity but if he’s not in it 100%, then it won’t be successful. It also won’t be fun for me. I just signed a new client yesterday who I have known for 10 years. He is smart, hard working, has a great existing business, and most importantly I trust him. We’re both stoked about working together which is a much better recipe for success. In the future, I can focus on pre-screening who I work with and invest time in.

2. This is what I signed up for: This situation is entrepreneurship in a nutshell. There is no guarantee of a paycheck every Friday. I get autonomy over my time but I have to earn it by dealing with the rollercoaster of emotions that goes into running a business. Yes, it was stressful, but stuff like this is always going to happen. I can handle this situation and recover from it. It’s just part of the game.

3. What can I do with this new time: While this feels like a setback right now to my income goals and “progress”, it’s very possible this is a blessing in disguise. Now I can focus more time and energy on my new client I’m excited about. Maybe that will lead to a bigger opportunity I can’t see yet. Maybe I can use my extra bandwidth to find a new client with even bigger upside. The great thing about entrepreneurship is that it’s not a zero sum game and the opportunities out there are endless, I just need to go out and find them.

This is just Part 1 of the Entrepreneurship Rollercoaster and I’m excited to continue on the ride.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew