A (Crappy) Week in the Life of This Entrepreneur

Ahhhh life as an entrepreneur. It’s so glamorous with things like not having a boss, money falling from the sky, being looked up to by everyone—not to mention the cars, the vacations, and, well, the life!

Okay, so if you’re an entrepreneur reading this you’ve probably already laughed. You know how sarcastic that statement really is. Anyone selling the story above is just selling a lie. At least—if that’s the only part of the story they tell.

Entrepreneurship isn’t all glitz and glam. It’s not just a life of success. Here’s a great image that brings it home:

There are various forms of this illustration out there. I’ll share another below in another context. But you get the point. We have an idea of what the path to success might look like yet it’s something very different in reality. C’est la vie.

This is entrepreneurship. We don’t start out with a plan to struggle to bring in revenue. We don’t plan to have conflict within the team. We don’t plan to fire people or lay people off. We don’t plan to be sued, or to have to close the business. These are all examples of very real things that happen all the time in business. But I’ve noticed that many entrepreneurs don’t like talking about these things. Perhaps out of a sense of pride; perhaps from the assumption that they should have known better and feel ashamed. Whatever it is, something often holds people back from discussing these struggles.

One of the things that brings me deep fulfillment is having raw conversations with entrepreneurs experiencing hard times and simply supporting them through it. I’ve been through some exhausting and emotionally draining seasons with my digital agency, Focus Lab. As a result, I can easily empathize with others going through similar seasons. In fact, I’ve shared some pretty raw details about my struggles over the years. Some of this I’ve shared from a stage at conferences. But most of it comes in the form of one-on-one conversations.

I had one of those conversations recently and it led me to share a journal entry with someone. I tend to write about my experiences as a form of helping me process what’s going on. As I was sharing this entry recently, I thought it might be helpful—to at least one person—if I just shared it publicly.

So, long story long, I’ve extracted an account of a 4-day period at Focus Lab from 2014. I logged this in my journal over a period of days and have revisited it a few times since. It was a time where our sales and revenue had slowed and we were faced with not being able to make payroll. And apparently the universe saw it fit to drop a bunch of other stuff on me that same week. Anyways, I’ve redacted a few small pieces of information but kept the majority of it just as it was originally written.

My hope is that this simply serves as a reminder or a revelation to other entrepreneurs that you’re not alone when you go through the crappy stuff. We all go through the tough stuff. Some more than others. So—here’s the account.

The week started with me knowing I had to come to a decision about potential payroll changes. We couldn’t cut expenses in any other area any longer. We were 9:1 in our payroll:other expense ratio. I got up at 4:30am and was in the office around 6am. I spent about 6 hours working. I knew I’d need to maintain a certain amount of separation from work thoughts so I left the office around noon and saw Guardians of the Galaxy (good flick) in a theater across town. I had some time in the car to listen to a non-business podcast on the way to and from the movie. After the movie I went back to the office for a few more hours of work, mostly on sales.

While working on some sales items, I got a voicemail from someone I knew from years past. He was looking for a developer — specifically an ExpressionEngine developer — to join his staff and replace someone who recently left. The role and the salary fit one of our team members to a T. It was a bit strange. God? Is that you?

We had a lot of good, small wins on Monday. Multiple verbal commitments to new projects. We knew we could expect a couple of signed contracts later in the week. Anything helped.

I went home around 5 and had dinner with the family. After I got the kids in bed I got back to work for a few more hours. I had a conference presentation on Wednesday and I needed to wrap up my preparation. I had tons of notes and needed to trim it down to a suitable timeframe. Then I chatted with Bill for a bit and we decided to email a bunch of clients we loved from the past 12–18 months. The plan was to let them know we were in a slower than normal season and could offer them a discounted rate for any work they wanted to put on the table. I wrote up a few email options and Bill and I talked through the merits of each approach. We decided what we liked best and emailed 9 people. I ended the night around midnight with time in scripture and journaling.

Tuesday was my daughter’s first day of 1st grade, so my wife and I both took her to school and attended the opening ceremonies for the year. I woke up around 5am, mostly just got ready and got the kids ready to leave. I made it to the office — after the ceremonies — around 10am. I worked on a few other sales items and then had a chat with Bill about the cash updates. We basically had to finally talk about whose job was on the line if we didn’t bring in enough money over the next few days. That’s an incredibly crappy discussion to have. It was productive and insightful. But hard as hell. I spent the rest of the day preparing for the conference presentation more.

That morning and afternoon we started hearing back from the clients we emailed the night before. We were getting some small interest and were pleased with that. Cash. It’s good.

Around 5pm I left for a local event where a non-profit organization we support was launching new office space. I didn’t want to go at all, but I’d committed to a few people that I would be there. Ultimately I did want to support them so I kept my commitment. I was exhausted and not in a social mood at all. I didn’t stay too long.

I headed home around 6:30. Then the usual dinner, showers, bedtime routine with the kids. After they were out, I spent time preparing for our full team meeting, our “Roundtable,” which was the next morning. I had to figure out how to best update our team with the facts of where we were. It sucked. Hard. How do you tell a dozen people that you don’t know how much longer you can pay them?

I ended the night with some journaling and hit the sack around 11pm.

I got up around 5am and ran through my conference presentation a bit more. Then I prepped once more for the Roundtable discussion. I was definitely not looking forward to that. The worst part — to me at least — was that I had to present the status of the company and then immediately go into my conference without being present or available to the team. That sucked. At the end of the Roundtable I shared two images. The first was Bill and I’s avatars in HipChat that we changed to remind our team that we were in a warrior mentality to fight our way out of the challenges we were facing.

Bill told me I did great with communicating everything to the team. I certainly didn’t feel great, but the affirmation was really helpful.

After Roundtable I moved into our Call Room for the digital conference. My talk was scheduled for 12pm. I was super stoked about it, ready, and energized. Noon came around and it was my turn to turn on my mic and webcam and get started. I got my setup all prepped, went to fire up my mic, and Flash wouldn’t let me “allow” it access to my mic. It just froze. I used the exact same setup during the tech check one week prior. I had no clue why this was happening.

I called one of the conference organizers on the phone and told her what was going on. I tried a separate browser but no dice. Thankfully I had a second computer nearby; one that typically stayed in that room. I fired up that computer after multiple failed attempts on my primary computer. I typed in the URL on the second computer and it said Flash was out of date (imagine that). So I updated Flash which took about 4 more minutes. All the meanwhile an audience is waiting for me to start a presentation on the other end. I finally got the mic and webcam running about 10 minutes behind schedule.

About two minutes in — while I’m going through some fun, ice-breaker style slides — the video and audio start breaking up and getting delayed. The software has a chat room where the organizers can tell me when something’s wrong. I saw their note so I paused a minute to let everything catch up. Then I continued. After a few instances of smooth video followed by chopped up audio and video the software completely froze up on me. So I called the organizer back and just asked her if I could bail on it completely. I had lost all interest in even presenting at that point. I had no “flow” to it due to the technical issues. Who could get anything out of an experience like that? So I proposed that I record a screencast of the talk while the other presenters were “on stage” that day. The goal would be for me to record, edit, and share the video by the end of the event, a few hours later. She liked the idea so I moved forward with that.

I didn’t want to record the talk in a single shot/take because the file would be too big to comfortably edit. So I hit record and started talking and switching slides etc. About 20 minutes in I stopped it so I could get some water and do the second half in a separate file. When I opened the recording I’d just made I realized that I recorded the video on the wrong screen. Not a single slide had been recorded in the entire 20 minutes. 100% waste / loss in terms of the recording. So I said, “Screw it. I’m going to lunch.”

So I went ahead and grabbed some lunch to clear my brain. A quick sub from Jimmy John’s did the trick. After a walk to and back from lunch I was re-energized and ready to rock. I filled up a glass of water, setup the recording stuff, and got ready. This time I decided to record in shorter segments; 10 minutes max each. I got through the first one and it was exactly what I wanted — so I was on a good path.

Then I reached for my water and knocked the whole glass over on the desk. In doing so I got water on 4 electronic devices, my laptop, phone, airport express, and an external HD, and also down the wall and into the power outlet. Oh — and into the power strip nearby as well. So I ran to get paper towels from our kitchenette nearby and got everything cleaned up. I sat down for about 10 minutes just to get over it all mentally. Then I dove straight back into recording the rest of the talk in small segments.

Now — I think — I can finally enjoy some of the talks. I had finally finished the video and uploaded it to our company Vimeo account.

About 10 minutes into the talk I’d joined, a team member knocks on my HipChat door and asks if we can chat about a specific project. He said a significant issue came up that afternoon. So we talked for about 30 minutes to hash out the issue and possible solutions. Then I got back into the event.

About 15 minutes later I receive an email from a support client whose website has been showing major performance issues over the past few days. Their site wouldn’t even load and it was up to us to fix it. The issue was in a hosting environment that we recommended and setup for them (rare). They weren’t livid, but certainly wanted prompt resolution, as they should be able to expect. I dug a little on that and passed it along to another team member.

Finally, back into the conference. I caught the last two talks in their entirety. Thankfully.

I took Wednesday night off from work stuff. I did take some time to tell Bill about the escapade of my day though.

I slept until 6am Thursday. You know, I needed some rest so I “slept in” a little. I took my daughter to school and headed into a meeting with our CPA at 8am. We looked at numbers and devised a plan to determine which team members had to be cut, if any, and when. That conversation sucked. But it was immensely helpful and I finally felt like I would be making an informed decision rather than a gut decision.

I went straight from that into an internal sales chat to discuss the various irons in the fire. We’d closed a couple of small sales already this week so things were looking a tad better. We also had some decent responses from the clients we emailed on Monday night. About $25k of potential immediate work just from those emails. Not something I’d usually get excited about, but this was great progress for us at this point.

At this point I’m doing everything I can to keep morale as high as possible across the team. I asked one of our team members to share in our “Water Cooler” chat room each time we signed a contract this week. That was adding some excitement which was good. At least — it looked like excitement. It was probably just a glimmer of hope everyone could cling to with each passing day.

Thursday afternoon I had a call with someone we were hoping would become a strategic partner in a new venture. The call wouldn’t bring forth immediate revenue, but had a ton of long-term potential. I left that call highly energized and excited about what we could do with this partner.

Late in the work day I got on the phone with a peer in the industry. We were originally going to talk about working together to solve a problem for one of Focus’ clients. That topic changed in the first few minutes though. As it turned out, his company was going through nearly the exact same scenario as Focus. Talk about crazy. It was nice to know we weren’t alone in this battle. We took some time to encourage and support each other. Then hung up.

I called Bill up to let him know a little about that call. I wanted Bill to hear and feel the same type of encouragement. While I was on the phone with Bill I received an email. It was a sales lead from one of the Creative Directors at [redacted well-known company name]. He said he’s been an admirer of our work for a while and just realized I’d been through [an event his company puts on]. They were hoping we could help them with an iOS design project they had coming up. Ho. Lee. Crap. Naturally I responded and setup a call for the next day.

Thursday night we had an open house at my daughter’s school. We went to that for a little bit and headed back home. My wife and I talked about our home budget and trimmed back everything we could so we could live out of our emergency fund for a few months until the company’s cash position was stronger. We’d officially decided not to take any money home from the company for a few months. Thankfully we had zero debt and 6 months of household expenses saved up in cash. We could make it. It would just be tight. We wanted to do everything we could to keep the team around as long as possible.

I ended the night with time in scripture, longer journaling, and listening to a good bit of worship music. Finally hit the sack around 12:30am.

There’s probably nothing revolutionary in the journal entry above. I just wanted to share an account of a crappy week as an entrepreneur. And it’s certainly not the only crappy week I’ve had. It’s just the one I was recently talking about with some folks.

Fast forward a bit from this journal entry, we ended up laying off some of the team. Fast forward a little more, and we recovered. I learned a few things from this, and similar, experiences. I’ll probably write in more depth about them eventually, but there is one particularly important thing you should remember.

You aren’t alone.

Entrepreneurship can feel lonely and isolating—particularly in the really tough times. But it’s important to know and remember that you aren’t alone. And if you’re thinking that your other entrepreneur friends and peers can’t relate to what you’re experiencing, you might be surprised at what you find out when you open up about it.

Success is not final, failure is not fatal: it is the courage to continue that counts.

— Winston Churchill

If you’re an entrepreneur in a crappy place right now, take heart! You’ll get through whatever it is in some form or fashion. And if you need to chat with someone in the meantime, just hit me up.