Friday marked the end of my twenty-eighth week of working from home (mostly). Here are my takeaways from week twenty-eight:

• Groove – This week, I felt like I was in a good rhythm and beginning to hit my groove. Looking back at my calendar, the week was busy with lots of meetings, but it felt less hectic. I’m starting to get used to this new pace and seeing early signs of balance.
• Giving back – I write daily, mainly in an effort to help others. This week I had conversations with five unrelated people who mentioned that my writings are helpful. This felt great! It was encouraging. I’m happy that others find value in my thoughts and experiences.
• Education – I participated in some meetings that educated me on topics I want to master. They reminded me how important it is for me to be intentional and seek out ways to continue to better myself and work toward goals I’ve set for myself.

Week twenty-eight was a busy week, but it didn’t feel as busy as it was. I’m looking forward to settling further into my new groove this coming week.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

I had a good conversation with a friend today. We both advise early entrepreneurs. Today we talked about things we’ve learned and best practices. Since we’re doing the same thing in different ways, we can help each other by talking through our experiences and sharing our perspectives.

One thing I’ve learned that I told my friend about has to do with asking versus telling. When you’re experienced, you can see things that novices can’t. When someone’s in a difficult situation that you’ve been in, the natural inclination is to help them avoid the pain that awaits by telling them what they should do or shouldn’t do. This can be helpful, but it’s not the best approach. You’ve set them up for future pain. Yes, you’ve helped them avoid pain today, but you’ve scotched their opportunity to learn. The next time they have to deal with something similar and you’re not around, they won’t know what to do.

When I work with entrepreneurs, I ask questions. My hope is that by thinking through the answer, they’ll connect the dots and learn something that will help them avoid pain both now and later. If I’ve had a relevant experience, I share it with them, of course. But my questions have been more helpful. I’ve noticed that entrepreneurs who’ve answered them feel like they’ve figured out what to do themselves, through learning, which is powerful.

If you want to help people, don’t spoon-feed them information—encourage them to reason . . . analyze . . . think. You’ll be fortifying them against future tribulations.  

Today marked the end of my twenty-seventh week of working from home (mostly). Here are my takeaways from week twenty-seven:

• Strained eyes – I shared my challenges with this issue last week. I received my blue-light glasses and they’ve helped tremendously. Despite having three multi-hour Zoom meetings (one for four hours!), I felt minimal strain on my eyes. This is a major change from last week and I’m thankful. I’ll continue to use the glasses and may order another pair as a spare.
• Writing – Writing quality posts was a struggle. I’m committed to writing every day, so not posting was never an option. I’m going to embrace the changes in my professional life and adapt. I hope that over time I can find the right adjustments to make daily writing fit more easily into my new schedule.
• Founder energy – I had a marathon of meetings with founders this week. The energy and enthusiasm emanating from these founders is encouraging and contagious. I’m hopeful I’ll have the chance to work with some of them as part of an investment portfolio.

Week twenty-seven was a busy week but a great one. I’m relieved that I was able to reduce my eyestrain. I’ve been very worried about it.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

Today marked the end of my twenty-sixth week of working from home (mostly). Here are my takeaways from week twenty-six:

• Transition – This was the second week in my new role at Outlander. I’m doing a few things at once. Learning a new industry. Working with a new team. At a brand-new firm. All amid a pandemic. I don’t foresee any dull moments anytime soon. I’m excited about embarking on this journey and helping early founders.
• Strained eyes – My eyestrain worsened drastically this week, resulting in headaches. I had to step away from my computer for long stretches, which limited my productivity. I researched and ordered some blue-light glasses. I hope they help. I think my eyes are over this pandemic.
• Reflection – I had a few people ask about the new role (before I made it public) and how it came about. As I described the journey, I realized I wasn’t consistent and left things out. I felt like I was shortchanging those who were interested enough to ask. So I decided to think it through, document it, and share it. The process was more involved than I realized. Recording it for posterity took much longer than I planned, but I’m glad I did it. I hope reading about my journey of self-discovery is helpful to other people contemplating major life changes.

Week twenty-six was a hectic one. I’m pretty worried about the eyestrain issue. I hope I can figure out a solution quickly. Otherwise, work will be very challenging.      

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

Today marked the end of my twenty-fifth week of working from home (mostly). Here are my takeaways from week twenty-five:

• Holiday weekend – I’m excited about having some downtime. I wish we weren’t in a pandemic so I could spend it with family and friends. Regardless, I’ll enjoy the time off.
• Time blocks – I’ve continued blocking out time on my calendar. I made progress on bigger projects. I’m improving!
• Giving back – I spent time giving back this week by talking with rising entrepreneurs, and I really enjoyed it. I’m looking forward to doing more of these talks.

Week twenty-five was a good one. It was very busy and I’m looking forward to a three-day weekend.    

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

Early in my journey building CCAW, I kept a notebook. I wrote everything down. It was a catchall of sorts for whatever was on my mind. Projects I was considering. Daily priorities. Problems I was trying to solve. Meeting notes. You name it. I recently came across one of these journals and spent time reviewing it. That particular one is about seven years old.

Reading it reminded me of many long-forgotten details. I got a glimpse of my entrepreneurial thought process back then. I laughed as I read some of the entries. Some of the challenges I considered big at the time paled in comparison to obstacles I would face years later.

Entries detailing the pros and cons of big decisions I was considering were very revealing. They gave me insight into the way I made decisions then. With the luxury of hindsight, I enjoyed evaluating my former self. I was spot-on about a few things, in the general vicinity for a lot of things, and way off the mark (i.e., wrong) about a ton of things. Looking at my notes, I can see where my logic was flawed when decisions didn’t turn out well. And why it was sound when they did. I can see that my thought processes evolved. I was learning and making better decisions.

As CCAW grew, I stopped writing in my journals. I got really busy, and trying to keep up with a notebook annoyed me. I started using the notes app on my MacBook and iPhone instead. I really regret that. I wish I’d kept writing in my notebooks. And I should have taken more time to review and reflect on my entries. I think that would have supercharged the evolution of my decision making.

If you’re an entrepreneur or are considering entrepreneurship, consider keeping a notebook and reviewing it periodically. You just might accelerate your growth!

Today marked the end of my twenty-fourth week of working from home (mostly). Here are my takeaways from week twenty-four:

• Teamwork – I was reminded of the value of working as a team. No one person can be good at everything. But combine people’s individual strengths, and you’ve got a team that is! (Well, good at everything important to you, anyway.)
• Pace – The pace this week was closer to normal.  Busier than I planned, but slower than the past two weeks. I was more intentional about whether and when I scheduled meetings.
• Time blocks – I began blocking out chunks of time on my calendar to focus on bigger things. So far so good. Mornings are still my most productive time.  

Week twenty-four was a good one. No major takeaways this week.    

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

Today I had a conversation with a buddy about reflection. He’s thinking of reflecting more and learning about various ways to reflect. He’s looking for the one that suits him best. I’m a huge fan of reflection. Experience is important, but it’s reflecting on that experience that contributes to wisdom. I wasn’t aiming for this when I started writing earlier this year, but my daily posts have become a form of reflection.  

Here’s what I’ve noticed:

• Thinking – Coming up with a topic every day is hard. I’m forced to replay the entire day in my mind. What did I work on? Whom did I speak with? What did I read? I look for the most important thing and then think about it more. I consider it from different angles, do a bit of quick research, mull over relevant past experiences . . . whatever comes to mind. I try to connect less obvious dots and better understand my experiences. I usually (not always) uncover a nugget that becomes the foundation of my post.
• Writing ­– Creating the post is an important part of my daily reflection. It crystallizes my thoughts. It’s one thing to have thoughts in your head. It’s quite another to articulate them logically in writing. Writing helps solidify my learning.  
• Compounding – Identifying the most important thing that happened every day and making small adjustments in my opinions, beliefs, or decision-making is effective. The effect of compounding lots of small changes over time is huge.
• Frequency – I’ve found that daily reflection is ideal for me. The rhythm is perfect. I only have to think back 24 hours. If I had to reconstruct a week or a month I’d be bound to overlook something worthy of reflection.

My approach to reflecting probably won’t work for most people, which is understandable. If you’re interested in the idea of regular, intentional reflection, I encourage you to test a few approaches to find the one that works best for you. It’s something simple that can have a powerful impact!

Today I had a great conversation with an entrepreneur about training. He noticed while working in corporate America that retention is a big problem. Companies spend tons of money educating their employees. They want to introduce the latest and greatest thinking to help their teams be the best they can be. Unfortunately, the employees don’t have time to apply what they’ve learned. More than 90% of knowledge is lost because it isn’t revisited promptly.

I’ve personally experienced this many times. I attend a conference, read an article, or watch something online. The information is great, so I’m excited and can’t wait to put it to use. Then I get back to everyday life. The materials stay bookmarked on my computer or filed in a binder. Usually, I never look at either.

Retention isn’t a new problem, but I think it will become more top of mind for company leaders. With so many people working independently from home, I think companies will be rethinking not only how to promote retention of training but also how to deliver it effectively.

The entrepreneur I talked with has a great idea for a solution and I’m eager to see the customer feedback once he launches an early version of his product.  

Today marked the end of my twenty-third week of working from home (mostly). Here are my takeaways from week twenty-three:

• Eye strain – This week I had a record number of video meetings, including one that lasted four hours. My eyes feel a bit strained, which probably isn’t good. I’ll avoid screens this weekend (as much as possible).
• Virtual showcase – I attended my first event in a virtual venue: Square One Startup School’s Startup Showcase. The organizers had arranged networking via one-on-one conversations, a DJ, and even exhibition booths. I was impressed and would attend another one of these.  
• Pace – This week was another busy one. I’m looking forward to returning to a more normal pace next week. (Truly! Yes, I know I said that last week.)
• Large projects – I planned to attack some big projects, but I couldn’t find the concentrated blocks of time it would take. I’ve blocked out chunks of time on my calendar to try to prevent this from happening again.

Week twenty-three was hectic. I didn’t accomplish what I wanted to, which was disappointing. I’m looking forward to having some uninterrupted time to focus next week.    

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.