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.

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Mon­day

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

Tues­day was my daughter’s first day of 1^st 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.

Wednes­day

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.

Thurs­day

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.

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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.