Blog Perfect Day


Left unattended, our strengths can quickly become weaknesses.

How is it that we can see our friends’ problems clearly, yet our own problems remain impossibly complicated?

All your friends know she is a bad match for him. Or that he needs to stop drinking. Or that he needs tech help.

Yet when it is us, we think, “She is a great girlfriend,” I don’t drink that much,” and “my business is fine.”



The humility to listen and change.

Three skills for the modern world that are even more essential for the self-employed.

It’s estimated that the number of freelancers will grow from 60 million (2018) to 90 million (2028) and make up over 50% of the American workforce. 

Worldwide this means hundreds of millions of people will soon have to manage themselves. 

In the same way guardrails prevent motorists from driving off the roadway, we need guardrails to do our best work.

Why Guardrails? 

Left unattended, our strengths can quickly become weaknesses.

As an ENFP or “Campaigner” personality type, I see ideas and possibility everywhere. Every scribble on the blank page could be a million dollar, life-changing idea. I believe in my friends’ dreams more than they do. Even when it seems impossible or ridiculous, I take the first step.

Yet too often it is only one step. A month later, I’ve started two other projects but finished none. In creeps the doubt, followed by paralysis. Is this the best idea? Should I pursue another instead? The endless possibilities splinter my effort, leaving me right where I started.

We need guardrails to stay on the road, to keep our strengths just that… strengths.

We need to literally step outside of ourselves, whether that’s 10,000 feet above or pretending to help yourself as you would a good friend.

Imagine seeing yourself in the third person. In what environment would this person thrive? Where, when and why does this person fall off the track? What guardrails would keep this person moving the right direction? 

What Are Your Habitual Blind Spots?

Your innate preferences and blind spots are two sides of the same coin.

I highly recommend Do What Your Are to help you identify your personality type and blind spots.¹ You could also explore different personality types online here.

When I read about ENFPs, it was as if the authors knew me better than I knew myself. Their quote to describe ENFPs, “Anything is possible!” could have been my personal motto. 

The book perfectly described my biggest weaknesses too: difficulty focusing, poor practical skills, and a tendency to start many projects but finish few. Bingo!

What ENFPs must do to succeed is prioritize and follow through.

Guardrails for ENFPs: A Case Study

Once you know you’re blind spots, you know where to put guardrails. 

Below is what I have done to keep myself on track. I hope this helps fellow ENFPs and gets you thinking about your own guardrails.

Blind Spot 1: Difficulty Focusing, Easily Distracted

Guardrail 1.1: Keep goals front and center

My goals are posted on my bedroom mirror. They are also conspicuous in my daily and weekly reflections. This might sound like overkill, but it is exactly what I need to fence in my impulsive nature.

Guardrail 1.2: Limit number of goals and projects per time period

My rule is to never have more than three tasks, goals, or projects per time period. For example, never have more than three to do’s each day, or three goals for the year. Ideally, there is only one goal per time period. What absolutely must get done this week, month, quarter, year?

Guardrail 1.3: Work in time blocks i.e. 25, 50 and 90 minute sprints 

Scheduling and working in time sprints has been my number one antidote to distraction. I commit to one piece of work – whether writing, podcasting, responding to emails – for a minimum of 25 minutes. No phone, no social media, nothing else! I’ve found 50 minutes ideal to enter a flow state without fatigue. Perhaps this is biological or a result of my childhood education that broke classes into 50 minute blocks.

Your most important goals deserve a minimum number of time blocks / day. 

And setting shorter time blocks for tasks you hate can help you defeat procrastination i.e. “I only have to respond to email for 25 minutes.”

Blind Spot 2: Difficulty Following Through, Poor Practical Skills

Guardrail 2.1: Find accountability partners 

Joining a mastermind – a small accountability group – helped my business immeasurably. Once a week I’d have to tell four other entrepreneurs whether I accomplished last week’s goal. Group members also helped me think through my priorities. Again, outsiders can often see your situation more clearly.

Other forms of accountability could be reporting to mentors, advisors or a board.

Guardrail 2.2: Require deadlines and deliverables for ideas 

Deliverables and deadlines force follow-through and output. ENFPs tend to overthink everything, which leaves many projects unfinished. It’s hard to set your own deadlines. Therefore I seek out events that end in a deliverable, whether that’s a Startup Weekend or a group committed to making something over a weekend. 

Other forms this guardrail could take include: 

  • Publish one blog post / week
  • Do at least 200 pushups / day
  • Launch one minimum viable product (MVP) this quarter.

Guardrail 2.3: Hire people to do routine, detail, repetitive work

I’m embarrassed to say that only in my late 20s did I realize some people love to do administrative work, which I despise. I didn’t think I’d be able to find anyone to help me do web research and data entry. Yet dozens jumped at the opportunity to do so. Hiring people also forces me to build systems so value can be delivered without me.

Guardrail 2.4: Work with realistic, practical people

Being idealistic can be a blessing and a curse. I surround myself with practical, common-sense people to protect against the curse. In my first business we had three partners. When we started, two of us would obsess over business models, financial projections and company culture. Our third partner – a serial entrepreneur – pulled us aside one day to think like “Chinese business man” (said with fully racist accent). What materials do we need to design our shop? How much cash do we need for the next three months? Who will work the evening shift? He kept our focus on what had to be done right now. We would have never launched our business without him!

If You Were Responsible for Helping Yourself, What Would You Do?

I would tell Darren (myself) to pick a job where he regularly encounters the new. I would tell him to find a role that rewards spontaneity and creativity. He should use daily checklists to stay on track, and hire an operations wiz as soon as possible. 

I would tell him that he needs more deliverables and deadlines. I would advise him to report to experienced advisors with track records of getting things done. He should also consider getting investors so growth and financial return is made a priority. I would also encourage him to model successful ENFPs. What do they work on and who do they partner with?

As adults, no one will do this for us. 

Self-awareness. What are your blind spots?

Self-management. How can you design your environment so your innate tendencies are harnessed, and don’t work against you?

The humility to listen and change. We all have strengths and weaknesses. The sooner we can admit and design for these, the farther we can go.

Where and what are your guardrails?

Darren’s guardrails as an ENFP personality-type

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¹ The authors of Do What You Are offer 16 personality types based on four questions. Everyone falls onto one side of these scales.

How do you interact with the world and where do you direct your energy?
(E) Extraversion vs. Introversion (I)
(E) Are energized by being with other people vs. Are energized by spending time alone (I)
(E) Like being center of attention vs. Avoid being center of attention (I)
(E) Act, then think vs. Think, then act (I)

What kind of information do you naturally notice?
(S) Sensing vs. Intuition (N)
(S) Like to use and hone established skills vs. Like to learn new skills, get bored easily after mastering skills (N)
(S) Tend to be specific and literal, give detailed descriptions vs. Tend to be general and figurative; use metaphors and analogies (N)
(S) Are oriented to the present vs. Are oriented to the future (N)

How do you make decisions?
(T) Thinking vs. Feeling (F)
(T) Step back; apply impersonal analysis to problems vs. Step forward; consider effects of actions on others (F)
(T) Naturally see flaws and tend to be critical vs. Naturally like to please others; show appreciation easily (F)
(T) Are motivated by desire for achievement vs. Are motivated by desire to be appreciated (F)

Do you prefer to live in a more structured way (making decisions) or in a more spontaneous way (taking in information)?
(J) Judging vs. Perceiving (P)
(J) Like to make decisions and control vs. Like to live spontaneously and remain flexible (P)
(J) Seek closure vs. Avoid closure (P)

2 replies on “Guardrails”

As an ENFP, this is really accurate and I wish I’ve implemented more of these in my early life. But miraculously, being in grad school again with many other personality types has helped me find guardrails and so much support and inspiration. Having a 2 hour commute and 8.30am classes also helps a lot. Lol.

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