Hello Aspiring Chillers,

Where to Invest:

1. Education

2. Retirement Accounts

3. Stocks

4. Real Estate

5. Crypto

6. Buying a small business

7. Starting my online business

I have started a business but have not yet completed that journey like I have with other types of investments. I don’t have my total ROI or anything like that to share with you. Therefore, we are going to do something different again this week. I am going to have a dialogue with myself about my experience starting online businesses in the last year. We have 5 questions that I believe explain the life changes of becoming an entrepreneur.

(Mod) What words come to mind when starting a business?

(JH) I have to say that it’s not for everyone. I thought it could be for everyone when I started. I do not feel that way anymore. Some hardships are not for everyone. You should understand that before I dive into any of my answers today.

Getting into the actual question, I have 5 words that I think explain the experience more than any others.

• Opportunity

  • This is a double-edged sword. There are options aplenty, which means there is opportunity everywhere. Since that is true, it is also true that every opportunity you take closes the door on another. That is the opportunity cost of choosing one option over various others. The goal here is to understand that and weigh the options, but once you are ready, you just have to commit to one and not look back.

• Engaging

  • Some people think they work hard. I was one of those people; it’s not the same kind of hard as starting a business. You have to want it so badly you will give up literally everything else to focus on this one thing for a long period of time with no guarantee that it’ll work out. You have to convince those who support you that it is the right choice, even though it looks like it could fail at any point. You have to learn so many things you didn’t know you needed to know how to do. There is never a dull day that’s for sure.

• Frustrating

  • What’s the quote, “We overestimate what we can do in 1 year and underestimate what we can do in 10”? I feel this on so many levels. I thought I could start all of these things and just outwork my way to the top. I am still trying, but what became clear is that everything is a big project unlike at work when you have 1 big project a month, a quarter, hell, maybe even a year. Now, you have multiple big projects at a time that you are managing and doing all of the work for. So even when you make progress, you can’t feel it.

• Exhausting

  • I separate this from frustrating because one that one is mental and one this one is physical. You work long hours, at least until all of the systems are in place. Then you work long hours making sure those improve and are maintained. You can’t really turn it off, even if you walk away from the computer or whatever at the end of the “work” day. If you think of something at 9 PM, you take the time to explore the thought, write it down, and struggle with it for hours. You have to be ready to give it your attention whenever the inspiration comes, plus all of the hours that you were already supposed to be working.

• Freeing

  • Your schedule is yours. I explored being super free with it at the start but turns out I work best before 2 PM. So what do I do? I wake up, no alarm at least, but I generally get up early naturally, then I walk downstairs and I start solving problems. When am I done? Whenever I have something else I have to do or I feel like there is nothing left for me to contribute that day. At the very least, if I did it then, it would negatively affect how much I could do the next day.

(Mod) You left a fairly cushy, albeit a bit stressful, job to start this journey. How do you feel about that decision 1 year later?

(JH) Honestly, I should have left earlier or stayed longer. If I had left earlier, I would be further along in this journey, and I believe that the longer you are at it, the more growth and reward you will see. On the other hand, at the end of my tenure, I figured out how to coast that little bit more, and I could have stayed longer to be able to fund these projects more easily.

In that thinking, I realize that the point is that no matter when you leave, you can say, "Oh, maybe I should have done it this way or that way if I did it over, knowing what I know now." This can be toxic to do to yourself. With all of that, I know I left at the perfect time because that was the time that I left, and I can’t change that. There is NEVER going to be a “perfect time!” When you are ready, just jump and hope know you can figure out how to fly. (Then put in the work to fly!)

(Mod) What opportunities did you focus on and why?

(JH) I knew I wanted a few things from the opportunities, and I knew there were specific skills I wanted to use because I felt that I had an edge in those aspects.

• I wanted to be able to do it from anywhere.

• I wanted to be able to take breaks for extended periods whenever I felt the need…at some point, not at the start.

• I wanted something I knew I could do for 10 years and not hate it.

This led me to look at my skills and focus on using those to fill the above aspects.

• Writing

  • I think that this part is where I was smart about what I wanted and what I didn’t. I was never really a writer growing up. I was a math and science nerd, which makes sense for where I ended up with the other two skills. This one is how I can share those other skills with the world though. It turns out the world runs on communication, and so the better you are at that, the better you will be at whatever you do. This is the skill I work the hardest on day-to-day.

• Software

  • I spent over 10 years of my life becoming an expert level software developer. I have an edge in that space, and that is a major reason that I continue to do it today. I can do it from anywhere and any time, and as long as I do it well, there will always be money in it. Most importantly, it allows me to be even better at analytics.

• Analytics

  • This is where the math nerd takes over at times. Data drives everything, whether or not you are paying attention to it. That was true before the AI revolution or the tech revolution, hell, that was true before the industrial revolution. We all make decisions on probabilities every moment of every day, and it’s been like that forever. Being able to see those decisions and analyze or predict based on them is a ton of fun!

(JH) Did I successfully skirt that question and still give some good information?

(Mod) It looks like it to me, but I guess the audience can be the judge of that.

(JH) I think the real point is to find a few things you are good at and get better at them. Do that until you feel like you can’t improve more. Hint: you’ll never get there, and if you did, you are lying to yourself.

(Mod) What was your biggest fear in starting?

(JH) Really going for the jugular with some of these questions, my guy!

(Mod) That’s what our audience expects.

(JH) There are plenty that I contemplate.

• I think that most people have the same overarching fear of feeling inadequate. That one is hard to ignore.

• Impostor Syndrome, you know, you work or feel like you fake your way to the top of an organization, but now it is all on you. Tough to fake it now.

• You think you are smarter than you probably are. I am attempting to assume I am the dumbest person in the room at all times moving forward.

Those ones you wrestle with, but you can talk yourself into not feeling them most of the time.

In reality, there is only one that I truly feel every day, and that is fear of wasted potential.

As we have covered, you cannot fail as long as you never stop. So I know my fear and how to conquer it; I guess there is some solace in that.

(Mod) What advice would you give to someone who wants to take the leap?

(JH) In the great words of Nike’s Ads, “Just Do It!”. You will never know everything you need to know before you jump. You are just going to be playing the probabilities game anyway. Do your best to stack the odds in your favor, once they are, go for it. Some days will be tough, shit, a lot of days will be tough, but hell, some days will be euphoric, and you’ll never find that working for someone else, in my opinion.

If your first idea fails, then try the second one; you have an infinite amount of chances. You only lose if you give up and you only have to be right one time.