Startup challenges

IT Challenges of a Startup

For a Friday afternoon, I thought I’d do a little post-mortem on this week’s challenges which is a bit of an update from this post. Even though weekdays and weekends kind of blur into just a “bunch of days” to get stuff done, I do spend Sunday afternoons or evenings writing out the upcoming week’s goals. Last Sunday was no different – I had a great list of things I wanted to complete this week…

Issue #1

And then Monday morning hit – hard. I was off to a good start, until about 8AM. Then, for some unknown reason, I lost internet connectivity on my laptop. And only my laptop.  My iPhone, iPad and other devices were working fine. My laptop had wireless connectivity to the home network – just no internet connection. But I was able to ping sites outside my firewall – things didn’t make sense (to me). I rebooted the router and laptop, did a safe boot, disabled the laptop’s firewall, reset SMC and PRAM, etc, etc. And nothing worked. So after trying these things out, I decided to head over to a local company who provided me great support last year when my Mac got a virus or corrupted filesystem and I had to re-image my laptop (that was a painful experience). Unfortunately the shop closed early – I was out of luck. At this point I figured another re-image was in my (immediate) future so I backed up my laptop (a lesson learned earlier!). Since this was a “many-hour” activity, I worked on other things and started the backup.

The next morning, the backup was done. I rebooted my laptop for good measure. And I got internet connectivity back. Frustrating? Yes!  Happy it worked? Yes! Do I know the root-cause of why it wasn’t working? No…

Issue #2

So Tuesday I was back at it, trying to make up for lost time. All was good. Wednesday morning was going fine until I got the email “reminder” that one of my site’s domain was going to expire in a week. Well I’d actually been meaning to move that domain and the site over to another hosting company I had started using earlier in the year. But this reminder came quicker than I expected. So I reacted to it and decided to make the move – now.

First thing was to transfer the domain over from my current provider to the new provider. This is a multi-day process because domains are regulated and you can’t just casually move a domain around to different providers. There’s a process to follow. And I kicked it off. In talking with the service provider I was moving to, they said they offer free migration of sites. Awesome – let the experts deal with moving my content from one hosting company to the next. Life is good.

Well it turns out that they move content from other hosting companies but not the  hosting company I was using. Ugh! Ok, let’s stop the process. “Sorry, the request to move domains has already started” Oh no, this can’t be happening. So now I need to move my content to the new hosting company. It got worse and I’ll spare the details but at a high level I needed to export my site to the new hosting company. Except I couldn’t do it directly – I needed to FTP it. Well MacOS High Sierra no longer has FTP built in (you can’t make this stuff up!). So I had to install an FTP app. Done!

Thru the excellent tech support of the new hosting company, I was able to get my content over but there were other tech issues they couldn’t help me with. I needed to talk with existing hosting company’s tech support – but this was their one week in the whole year where they do their own maintenance, support updates, etc, etc. They had a “skeleton crew” working. So I was up a creek without a paddle as they say.

As luck may have it, on Wednesday night I got an email to confirm if I really wanted to move my domain name, yes or no. It was a quick reply “no”. I had a feeling of relief but it was short lived.

Issue #3

Thursday morning started out great. My website was up and running, life was good. But then a “what if” question got the better of me. I wanted to do an experiment. Since I had already imported my site to the new hosting company, I figured why not go to the old hosting company and point the name-server to the new hosting company. That would allow me to see what my site looked like with them as a host (so the theory goes). I should mention that with my plans of moving the site, I knew I needed to choose a new website template and make layout changes. As such, I wanted to go and see how much work it would be. My existing site was “safe” and all was stable so I figured it was low risk. Right…

Well it wasn’t. Once I added the name servers of the new host at the old hosting company, I couldn’t access the site. Ok, not an issue. I can fix that by removing the name servers I just added. Ugh – that didn’t fix it. And it got worse – when I typed in my site address, it got redirected to another site I run on the new hosting company. Not good.

So I reached out to the hosting company. But remember, their support team was a skeleton crew. Ugh. I sent in a couple of support emails, crossed my fingers, took a deep breath and waited.

Overnight I got an email saying what the issue was and they reset some configuration parameters. My site was back this morning. Yay!


While I lost a few days of productivity and the ups-and-downs of my stress level was a “major attraction” rollercoaster this week, here are some takeaways:

  1. As a small company, you don’t have all the resources or expertise to do everything in-house. So make sure you have a network of people who have the skills and expertise to help you out.
  2. Don’t dwell on issues. Do what you can, get others involved to help and move on. As the leader of your company you have lots of things on your action list. Work on those while you’re waiting for fixes to be implemented. You can almost think of it as delegating to your virtual team. Not dwelling on it will and working on other task will do three things for you: 1) you’ll get some things done that you might not have otherwise gotten done and 2) it’ll pre-occupy your mind (important for me) and 3) it’ll give you a sense of accomplishment.
  3. If you can, have backup or standby equipment. I’m looking to buy a new laptop later this year and will keep this one. Just in case…
  4. Take a breather and get away. Either waiting around or taking initiative to figure it out yourself (isn’t that what entrepreneurs do?) can drive you crazy. I actually went running a few times to release tension. Take a break from the issue
  5. Learn from the experience and let it make you stronger and more resilient.
  6. Remember it’s not the end of the world. Put things in perspective. You’re doing something to help others. That’s your mission. There will always be some hurdle thrown in front of you. But keep to your mission and it will all work out in the end.

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