Make Better, Braver Decisions with an Investor Mindset

May 7th, 2016 — 6:00am

This article was originally published on The Mogul Mom.

Investing, in the broadest sense, is the practice of choosing your present actions intentionally to produce the results you want at a later time.

Financial investors buy stocks and bonds now, in hopes they will be worth more at a later time. Entrepreneurs invest effort and capital now believing the businesses they create will deliver rewards in the future. Parents invest their energy and resources now, doing their best to ensure today’s children will become flourishing adults years down the line.

A future-driven, investor mindset guides hugely-rewarding decisions, but it is not a natural way of thinking and acting for us humans. The sensory experiences and emotional poignancy of the present moment are powerful. Our biology and neurology urge us to focus on surviving today over maximizing tomorrow.

A Ugandan friend of mine leads a charitable organization that helps farmers in his country produce more crops and get them to markets more efficiently. When the org was brand new I talked with him from time to time and heard updates on their progress. Distribution of superior corn seed and education on farming methods were successful, and the crop was looking good. The amount of corn produced was twice what the same farmers had grown on the same land the season before. We were so excited about how these farmers would benefit.

The time came to harvest the crops, and the harvest was a success. The employees of the organization rented a truck to transport the crops from the remote rural area to markets in the city.

When the truck arrived at the farms, they found no crops there to pick up! My friend was dismayed to learn that the farmers had already sold the crops from their big harvest. A local crop trader had offered them half price to buy the crops now. Rather than waiting a week or two for the truck to arrive, take the crops to market, sell them, and then pay them, the farmers accepted the cash-in-hand offer. They gave up all the benefit they would have gained from the higher yields that season. As you can imagine, my friend was extremely disappointed that the increase he sought to create was lost.

It’s easy to feel we would never do what those farmers did, that we are exempt from making such short-sighted tradeoffs. Not so fast.

Think about the pressures they were under. What if the crops never made it to market, or the money from selling them never made it back? What if the crops were stolen before the truck arrived? What if the nonprofit organization couldn’t be trusted? Their families might face starvation. Selling for half price, cash in hand right now, ensured their family’s survival for another season. Sending those crops to market for full price didn’t.

We are hard-wired this way. We all make decisions that are very much like their choice to sell their crop for half price.

An unfulfilled worker might choose another day at a job that promises to pay the bills, but returns “half price” or less on his or her true career potential.

A business owner might choose to spend an afternoon’s free time on routine tasks, avoiding the uncomfortable uncertainty of the big-picture strategy work that would more than double sales.

A married couple might choose another day of polite co-existing in a “half price” relationship, when confronting and resolving what’s broken between them might multiply the rewards of being together.

When the pressure is on, when fear looms in us, our instinct is to prioritize safety and survival even when it means our long-term future will take a hit.

So how can we be unnaturally wise, cultivate a long-term investor mindset, and make better, braver decisions? It can be done. Great investors develop a strong sense of the future. They feel it vividly, and this informs the decisions they make today.

A few suggestions:

Schedule periodic times (no less than quarterly) to direct your attention to the future. Bring that “later time” into focus by exploring and reviewing your vision, your big goals, and the rewards that make it all worth it for you.

Write your long-term goals in succinct statements. Map out plausible paths to achieving those goals. Refer back to these for clarity when things get hectic.

Bring your best mentors and your best friends into this with you. Talk with them about what you want most. Getting the future out of your head and into an audible conversation will make it feel more real and attainable.

Run the numbers. Make a spreadsheet showing the likely long-term returns from that expensive hire, that project to increase recurring revenue, or that additional allocation to your retirement account. Math is remarkably unphased by our short-term biases, and can lend clarity and confidence at decision time.

Put the next steps toward your long-term priorities into action now. The pressures of life and work will always be there. Waiting until you feel caught up and comfortable isn’t realistic. Let some other things slide to make room for your long-term priorities. That’s a good trade.

Some questions to ask yourself, and explore with those who support you:

What do I want most in the future?

What scares, distracts, or pressures me away from pursuing that?

Where am I choosing “half price” today at the expense of the future I want?

What could I do today that might not be obvious, urgent, or easy, but would make a big impact over time?

Are You Running in the Right Direction?

April 7th, 2016 — 5:00am

This article is adapted from Chapter 1 of Investing With Purpose and was originally published on Money Q&A.

Life and work, they ask a lot of you. There’s a lot to be done, and some of it is really hard. Projects stretch your skills, packed days stretch your energy, and difficult people stretch your sanity. Some weeks (most weeks?) feel like marathons with a series of embedded sprints. You get tired, and you have to stop to catch your breath sometimes.

Not to worry though, you are no stranger to hard work. You’re driven, even when it gets tough. You focus your smarts on each problem, and most of the time you work out a solution.

You do your best to manage your money, save for the future, and invest well to grow it. The enthusiasm and perseverance you bring to life and work is admirable, it really is. You have your ups and downs, of course, but you put your heart into it, and engage each day in an earnest pursuit of… well, hmm.

Illustration by Ian Riley

Illustration by Ian Riley

It’s for success right? Financial security, that is important. Maybe it’s about earning respect, and a sense of accomplishment? Being able to go to bed at night feeling like things are going ok, people see you and treat you well, and life is just kinda, working?

Ok, so life gets a little murky, even for us driven types. It’s hard to discover and remember why we are doing all of this in the first place.

What’s more, life changes and unfolds in surprising ways. We find out we have interests, strengths, potential we didn’t know about before. Windows of opportunity close (sometimes slam quite rudely) and others crack open. What we want changes. A clear sense of direction doesn’t come easily in the first place, let alone update itself automatically.

You can navigate life with direction and purpose. It’s possible, and it’s essential. A crystal ball of insight into the future is not required.

Courage, that is the thing. Courage to open up big questions and let them bother you with their annoying tendency to hover around unanswered. Courage to spend time in the part of you where you keep your dreams.

What do you really want, more than anything in the world? What are you telling yourself you will get around to, someday? What is your gift to the world, the difference you are aching to make?

Who matters most to you? And if you could tell all your raucous self-doubts to just zip it for one minute, what voices of aspiration would step cautiously out of the shadows and quietly speak their stories of possibility into the microphone?

Such questions are maddening to some, and deep-down-terrifying to all of us. Lean in. Explore the answers to those questions, bravely and persistently. Bring your best mentors and best friends into the fray with you. Keep exploring, keep pushing back the murky fog, as life twists and turns.

Reflect before you race. Then go. Infuse the answers to those questions into all your decisions. Enter yourself in the races that lead to what you want most. Risk wanting things, important things, that you might not get. Run. Run hard. Manage, save, and invest money with all the savvy you can, and use it to power what matters most to you.

There’s nothing more thrilling than crossing finish lines you barely dared to dream about. Invest each hour and each dollar intentionally, with your chosen direction and driving purpose in mind.

What you want is more attainable than it seems. Courage, that is the thing. Invest well.


Getting Tired

January 27th, 2016 — 10:54am

Between the inspiring goals, smart strategies, and effective things we want to do, there’s another, less-published reality. We all get tired.

A mountain hiker dreams of the breathtaking vistas she’ll see while standing on the peak. Inspired by her vision of that moment, she parks her car at the trailhead and starts enthusiastically up the trail at a jog.

An hour later, she’s tired and her steps are slowing. The trail was steeper and muddier than she expected. She realizes breakfast wasn’t nourishing enough for this kind of workout. And the distance to the peak is starting to feel overwhelming. As a driven and hard-working person, maybe she feels like she should push on and drag her tired self to that peak.

Her best move in that moment is probably to stop, sit on a tree trunk, enjoy a cool drink of water, and eat some energizing trail mix.

We are all hiking mountains of one kind or another. We all get tired. We aren’t made for long-distance mountain-sprinting on an empty fuel tank. Take breaks and take time for what refreshes and re-energizes you. You’ll enjoy the journey more and cover more ground in a day.

My Strikeout in Trucking

December 15th, 2015 — 5:30am

In 2013 I hatched an idea for a software system to deeply analyze over-the-road trucking dispatching for optimum load selection and scheduling. In a two-week bleary-eyed marathon of coding I created a working prototype. Exhausted, and satisfied that it worked, I set it aside.

In 2014 I was looking for investment opportunities and I decided that trucking software was one of the best I had laying around. I spent a good portion of the 2014 year-end holiday season turning the prototype into a usable beta version. I intended to put a truck on the road to use as a research and development “guinea pig” for the system.

Around that time I landed my book Investing With Purpose in a publishing contract. With much reluctance, I put trucking aside for another eight months. I poured myself into writing the best darn book I had in me. In August I turned it in.

Then I went into motion. I hired an experienced trucking business manager, and we began filing all the paperwork required to operate as a common carrier. I worked on the software between other responsibilities, and the pieces started coming together. Unfortunately the manager I hired didn’t work out in the role, and I terminated her employment. We were mid-project, and I decided to carry it forward with the help of my assistant.

The Truck

The Truck

And we did. We completed the paperwork, bought a truck, hired a driver, and got the thing rolling. I scrambled to adapt the software to the needs of the business on the fly. My system worked as I hoped it would. It was a thrill to see this two-year-old vision come into being.

At the same time I began to realize my system just didn’t fit the way the people of the trucking industry actually work. Several people had warned me in advance about dishonesty, unreliability, and rule-breaking in the trucking industry. They were right. Information flow from brokers about loads, rates, and schedules was limited and inaccurate (or even falsified). I also discovered that harsh verbal pushing and shoving were standard practice whenever a problem or sticky situation arose with a booking or delivery.

Not only is my software incompatible with that environment, I am incompatible with that environment. On several levels.

When all of that started to come clear, I had to grapple with disappointment and a sense of failure. My big dreams for that software were changing to nothing but big problems. I had never “struck out” on a business endeavor before, which meant my perfect batting average was going up in smoke. I imagined peeling our shiny new logo off the truck. I didn’t like it.

Continuing longer wasn’t going to make anything better. I made the call and pulled the plug. I called my driver and told him we were shutting down. We filed paperwork to end a business. I’d never done that before.

The same day I made the call, I started to think about what I want to swing the bat at in 2016. I had (irrationally) feared I would never find interesting new possibilities to replace that passion project. I was surprised how quickly ending one thing made room for creative thoughts of the future.

Since my batting average will never be a thousand again I guess I can let that go. Maybe there’s even a little relief in that. I feel surprisingly un-devastated.

I think the lessons learned from this excursion were worth the time and money they cost me. Here are a few of them:

  • It’s really hard to swim against the current of culture. Behaviors, values, and worldviews engrained for decades (even generations) can overpower individuals, innovations, even economic forces.
  • Corruption is a real thing. I knew that conceptually. Now I know it experientially. I like to think the best of people. Reality isn’t that simple.
  • Engineering a solution that works does not guarantee a business that succeeds. I’m going to keep this lesson close at hand in my future angel investments. Yes, the product or service must function as envisioned. It also must be accepted and paid for by people. It’s probably more important to understand the worldview and patterns of behavior of those people than to understand the engineering of the product itself.
  • Starting small really is a good idea. I had considered buying an entire trucking business to develop my software alongside. I’m glad I stuck to my belief in lean startups and minimum viable product.
  • Sometimes cautionary tales are true, and there’s still value in finding out for yourself. There’s always someone who says “that won’t work”. In this case they were right. In most other cases in my career, they were wrong. Trial and error is a good way to tell which is which.
  • The attempting process is valuable in itself. Success at the original objective is not the only reason to attempt something. I like success better than failure. At the same time, the process of attempting to manifest something brings much learning, and awareness of new opportunities. I’ll remember lessons learned for the rest of my life, and I could list at least a dozen business ideas that this trucking venture sparked for me.
  • Trust the abundance of the unseen future. There will be new to replace what you let go of. New ideas, new relationships, new projects, new inspirations. Accepting (even causing) the end of one thing is a good way to make space to discover what’s next.

P.S. Anybody wanna buy a truck? :-)

An End to Weekly Blogs

September 3rd, 2015 — 5:30am

Every week I hear from one or two people who found value in my blog post. I’m really grateful for the chance to share my thoughts and experiences and help a few others in the process.

At the same time, the truth is the reach of my blog is small. It hasn’t caught on, gone viral, or anything of the sort. Alas, mega-blogger I am not. When I evaluate the return on investment (impact per hour of my time), it doesn’t make the top list of most impactful things I do.

In my book I preach ROI. I advise the reader to focus resources where the greatest returns are. It’s time for me to practice that. My foci in coming months will be the book, the Leadership Development Cohort, Sunstone Transportation, the acoustical products business, and the a/v rentals business.

I’ll probably post a few times per year, maybe more someday down the line. Thanks for reading. Over and out for now.

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