Schlaf.me

“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.” -Meg Wheatley

The holiday season is my favorite time of the year. It symbolizes family, friends, vacation and of course plenty of good food. I also enjoy it because it marks the end of the year and the beginning of a new one. This is an ideal moment to reflect on the past twelve months and to define what we want to achieve in the year ahead.

So much happens over the course of a year. Lessons learned. Victories. Hardships. Physical changes. Special moments. Personal growth. New relationships. But by the time New Year’s rolls around, we often forget most of what happened because life gets in the way.

Many of our employers have us complete an annual review and set goals before year end. This makes good sense. It’s difficult to know where to head if we don’t know where we’ve been. But this leads me to the question: why don’t we conduct an annual review for all the components of our life? The answer is simple: we don’t create the time necessary, feel any pressure to or have a blueprint to guide us.

For the last three years, I’ve carved out time at the end of the year to conduct a comprehensive annual life review. The process has been not only cathartic but also illuminating and empowering. In fact, this exercise has helped me identify what’s important, shed what isn’t, and transform in many ways. As a result, I decided to get sober, leave a job that wasn’t the right fit and pursue coaching as a profession.

Several clients and friends recently asked me to share my annual life review blueprint. What follows is an attempt to provide the framework and hopefully the nudge to complete your own annual life review.

Setting the Stage

First, I recommend giving yourself a week to complete the entire process. Don’t try to breeze through the exercises in one sitting. Make sure you have time to carefully review, internalize and complete the exercises. In fact, I recommend blocking out several 30–60min if you can make that work. I typically complete my own annual life review between Christmas and New Years. I find this week tends to work well because many of us are away from the daily grind and have ample downtime.

Second, I recommend creating your ideal environment for deep, focused work. Power down your devices. If you are using your computer, I suggest turning off wifi and quitting your web browser. Find a comfortable place that you find suitable for work. Perhaps you’ll need a pair of headphones and relaxing music. I also recommend having a notebook by your side to take notes, brainstorm and capture anything that comes up during the process. You know yourself better than anyone. Do what it takes to get into the flow.

Third, be genuine. Be bold. Be selfish. Be completely honest with yourself. This is for you. No one else. You will get what you put into it.

Finally, this framework is not meant to be prescriptive. You can move sequentially through the four steps or just focus on a few. If you don’t feel like answering a question, skip it and continue. You are in charge here. This is for you. You will get out what you put in. Remember that.

All that said, I can’t promise this framework will help reveal the meaning of life or solve your biggest problems. Here’s what I do promise: you’ll end the year with way more perspective and have a compass for what you want to achieve next year.

In closing, best of luck on your journey. I hope you find these exercise to be thought provoking, empowering and motivating. At any point in the process, feel free to email me at steveschlaf@gmail.com with any questions, comments or feedback. I would be delighted to hear form you. Good luck!

Your Annual Life Review Blueprint

Step 1: Plot Your Moments & Milestones

I always start my annual review by making a timeline that plots the major moments and milestones from the current year. In order to kick-start the process, I first review my calendar to recall what happened and then see what other events, moments, etc. come to mind.

So what could be included as a moment or a milestone? That is entirely up to you. Remember this is a personal process. You can incorporate a range of activities, actions and accomplishments. Below are some ideas to help stimulate your memory.

Did you? Complete a course. Take a big risk. Create a new habit. End a relationship. Fall in love. Make a new friend. Get an award or promotion. Take a memorable vacation. Visit a new city or country. Change professions. Get married. Learn a new skill. Launch a company. Move apartments. Fail at something. Achieve a big goal. Start a family. Visit a museum. Attend a big game or concert. What were the big moments and milestones in your life?

Any timeline will work. I typically use a vertical one. If you prefer a horizontal timeline that is ok. Do whatever suits you. The format doesn’t matter as much as the moments and milestones that you plot on your timeline. Here is a simple template I created:

And is here is my timeline for the current year:

It should go without saying that my example isn’t comprehensive but hopefully it provides a sense of what your timeline could include. Once you have your annual timeline, it is time reflect on the past year.

Step 2: Reflect and Examine

This is where the real fun and work begins. Below is a series of questions designed to help you reflect on and examine what you experienced this year. Prepare mentally and emotionally to look at your successes, failures, relationships, lessons and themes. We’re going to cover a lot of ground. Remember to take your time, be honest and enjoy the process.

Success & Growth

• What were your two or three biggest accomplishments / successes? What contributed to them?
• Are there any other goals you achieved that you are you proud of?
• How did you grow over the past twelve months? What’s different?
• What are some healthy habits you integrated into your life?
• What are some new skills you developed?
• What were the biggest obstacles you overcame this year? What happened?What internal and external resources did you use use?
• What were the two or three best decisions you made all year? What did you learn from those experiences?
• What risks did you take and what were the rewards?

Failure & Falling Short

• What were your biggest failures? What did you learn from them?
• What goals didn’t you accomplish? What got in the way?
• What were some bad habits you followed or adopted?
• What were the two or three worst decisions you made this year? What did you learn from them?
• What do you wish you accomplished this year? What can you do about this next year?
• Where did you spent too much time or other resources?

People & Relationships

• What new relationships enhanced your life? Who? How?
• What single person had the biggest impact (positive or negative) on your life? How?
• Which relationships do you value most personally and professionally? What is it about these people?

Lessons & Themes

• What were the top lessons that you learned this year?
• What were the two or three peak moments this year? What were you doing? What did you learn?
• What were the two or three lowest moments this year? What happened? What did you learn?
• What five to seven words describe this year?
• What are you most thankful for?

Step 3: Assess Your Life Right Now

I’ll say it again: it’s difficult to know where you are going if you don’t know where you are. For this step in the process, you are going to assess your life across ten dimensions. These dimensions, taken together, represent a lens to help you look at your life holistically. This exercise is a slight adaptation to the self assessment tool known as the ‘The Wheel of Life.’

I’ve created a ‘Life Assessment Board’ to guide you:

This assessment captures your satisfaction in the major areas of your life. It should be a current snapshot. Don’t worry about how you felt earlier in the year or where you want to go in the future. Reflect how you feel you about each dimension right now. The purpose isn’t to make you feel deficient or lacking. The goal is to help you see where you are/aren’t satisfied and then to help you find more balance.

Now to the scoring system. Assess your satisfaction in each dimension by giving it a value from one to ten. A score of one means “Highly unsatisfied.” A score of ten means “Couldn’t get any better.” Remember to be honest with yourself. Your board should accurately reflect how your feel about your situation.

Here are some questions that might help you assess your life in each dimension:

• Health: How does your body and mind feel? This includes energy, nutrition, sleep, exercise, mood, mental health, etc.
• Family / Friends: How do you feel about the quality of relationships in your life? This includes family, friends, co-workers and how you communicate with them.
• Love: How do you feel about romance in your life? This includes connection and communication with loved one(s), intimacy and sex.
• Money: How do you feel about your financial situation? This includes income, expenses, debt and financial freedom.
• Career: How do you feel about work and your career trajectory? This includes your current role, career strategy, industry, work/life balance, co-workers, power and status.
• Spirituality: Are you connected to something bigger and greater than yourself? This includes religion, beliefs, rituals, practices, meditations, and expression.
• Personal Growth: How much time do you devote and spend towards self-improvement? This includes reading, training, learning, writing and coaching.
• Fun: How much time do you devote to recreation and fun? This includes events, shows, travel, time outdoors and anything you consider fun.
• Technology: How does technology play a role in your life? This includes your relationship to devices, time spent online and ability to disconnect.
• Environment: How do you feel about your physical environment? This includes your living space, country, city / town and workspace.

This is what my self-assessment board looks like as I head into 2019.

The purpose of this exercise isn’t to score a perfect ten across the board. Instead, the goal is finding balance and achieving satisfaction in each dimension. You should be able to see where you are out of balance. That knowledge is power. And with knowledge and power, you can choose how you would like to move forward and make changes.

To take this exercise one step further, look at the dimensions and ask yourself which area(s) do you want to focus on in the coming year? Try to focus on no more than two or three. That way you can remain laser focused. For me, I need to focus on my phone addiction next year. This is a problem which adversely impacts my relationship and productivity. I hope to make some positive changes in this category.

Step 4: Plan For The New Year

You’ve made it to the final step! It’s now time to define, visualize and plot where you’re heading in the new year. Who do you want to become? What do you want to achieve? What resources do you need? Who is going to be a part of your journey? You’re going to dive into questions like these and more. At the end of this stage, you will have more clarity and a plan to get the most out of your life in the new year.

Goals & Growth

• What three big goals will you accomplish next year? What’s important about them?
• What two or three skills / competencies will you acquire?
• What is one superpower that you will utilize to achieve your goals?
• How do you intend to be different by the end of next year?
• Who do you want to become?

Moving On

• What do you want or need to shed?
• What no longer serves you?
• What do you need to walk away from?

Habits & Behaviors

• What are two or three habits or behaviors you will stop?
• What are two or three habits or behaviors you will start?
• What are two or three habits or behaviors you will continue?

Fears + Obstacles

• How will you step out of your comfort zone and face your fears?
• What obstacles will you face and how will you overcome them to accomplish your goals?

Relationships

• Who in your life deserves more attention?
• Who do you plan to build a new relationship with?
• Who will you mentor and help?

Next Steps & Planning

• What are the next steps you can take towards your goals? Be specific!
• What resources do you need in order to start making progress?
• Who will you seek help from?
• How can you crate early wins and momentum?
• How can you evaluate your progress?

Several weeks ago, I was introduced to a talented young man who, like me, is passionate about personal growth and technology. He has been developing a new system grounded in research to help people drive change in their lives personally and professionally.

Before our video call, I visited his website, twitter feed and his other online profiles, only to discover he has not shared much over the years. I could not see what interests him, what he thinks about, and what he values.

While we were talking, I thought to myself, ‘This young man has so much knowledge to share with the world and could help others yet he isn’t using any digital tools to distribute and amplify his work.’ I wondered why this was the case so decided to ask him.

His response was short and simple: “I haven’t found my voice.”

This hit me hard because voice is expression, voice is communication, voice is creation, voice is confidence and voice is power.

Over the last few weeks, the phrase, “I haven’t found my voice” has been echoing in my head. I believe this young man wants to share his ideas badly but there is something getting in his way. He is not alone. There are thousands of people out there who want and deserve to be heard. Once I realized this, I began to ask myself, how does one find his or her voice?

I have been reflecting on that question for the past week. Here is what came up for me based on my experience and a number of conversations with friends.

1. Believe in yourself just enough to get started: when we start anything, whether it is riding a bike or recording a podcast, the initial step is often the hardest because we feel awkward and might not have command of the skill or craft. Ignore your inner critic that is trying to hold you back. Believe in yourself and just start.
2. View your work as practice: Every essay you write, every class you teach, every workshop you facilitate, every picture you take, every video you record, every podcast you broadcast is practice. Practice, practice, practice. You can always start over tomorrow. Creation is a practice.
3. The medium matters: Select a medium that excites you, challenges you, fits into your routine, feels native to you, and allows you to fully express yourself. Experiment. There are a range of online mediums: Twitter. Instagram. Snap. Medium. WordPress. Podcasts. YouTube. And remember you don’t need to find your voice online. You might be more comfortable conversing, teaching and facilitating in person. That’s ok! Go for it. Remember, not everyone is born to thrive on every medium but we all have the means to test these mediums and discover which ones align with how we want to communicate with the world and share our ideas.
4. Listen to your inner voice, not your inner critic: Your inner voice often knows exactly what wants to emerge but too often our inner critic gets in the way. If you are inspired to use your voice and create something, give that voice more weight than the other one telling that you’re too busy, not good enough or don’t know what you’re doing. Follow the inspiration.
5. Be patient and persistent: Finding your voice will take time. People work hard to find their voices and hone their craft. This doesn’t happen over night. And you will likely not feel comfortable at any step in the process. Here’s the good news: if you invest a 15–30 minutes each day, the results will follow. You will create momentum. I have no doubt.
6. Be genuine: This one is critical. Don’t emulate someone else. Be yourself. Develop your own tone. Follow your values. Follow your interests. Follow what you truly care about. If you honor who are, what matters to you and what you are truly passionate about, your voice will be distinct and it will show.
7. Don’t compare: If you are recording an interview series, do not compare yourself to Larry King. If you are writing a short story, do not compare yourself to Stephen King. If you are starting a blog, do not compare yourself to Fred Wilson. If you are starting a vlog, do not compare yourself to Casey Neistat. You get the point. Instead, focus on your voice, output and weekly small improvements.

This all is easier said than done. I struggle with writing even though I want to express myself through this medium. I definitely have not invested as much time as I would like but I am trying. In fact, I recently blocked out time on my calendar each week to write. Additionally, I badly want to publish a podcast on leadership but I have not taken the first step. I am aware of this which is the first victory. Creating and finding our voices certainly is not easy but I know it is possible if we invest the time and make it a priority.

I will end with this. It does not matter if you have an audience of one (you!) or an audience of a million. There are people out there waiting to hear (and see) your message. Being heard and seen is a fundamental human desire. Remember that. Follow your inner voice and heart. Speak up. Share. Ignore your inner critic. Let the world see and hear you. We all have something to say and contribute. Now go find and hone your voice. Good luck!

I’m thrilled to announce that I’m joining Primary Venture Partners as a Venture Partner. Over the last six years, Ben and Brad have been co-investors, thought partners and friends. Ever since the fall, they have been helping me think through a number of paths I have been exploring. That discussion evolved over many months, to the point where it became clear that we had a lot to gain from each other. This started as a super casual, “Hey, why don’t you come hang out for a while,” thing and evolved from there to the point where we realized it made sense to combine forces.

Ben, Brad and the rest of the Primary team are arguably building the most hands-on and operationally minded Seed fund in NYC. They do not spray and pray. They are active, high-conviction lead investors, and they care deeply. They are also focused exclusively on NYC, which was a huge factor in my decision. Everyone at the firm deeply believes in this ecosystem, and that is reflected not only in their strategy but also in how they are building the firm. Most importantly, everyone around the table has operational chops, strong values and a real desire to help NYC founders build impactful companies.

As I have peeled back the curtain and talked with founders in the portfolio, I have been blown away by the Primary platform. The firm’s Portfolio Impact Team, comprised of dedicated Talent, Finance, Market Development and Communications pros, is designed to support companies from whiteboard all the way to Series A and beyond. Additionally, the Primary Expert Network, a network of over 200 seasoned technology operators and functional experts, helps founders solve their most pressing tactical problems. They’re just getting started, too. Many firms these days claim they have a platform, but it’s often just “checking the box.” Not Primary. They’re investing aggressively and playing the long game to build a real franchise here in NYC.

Many people have asked me, “So what is a Venture Partner?” The title means different things at different firms. Here’s what I’ll be focused on: My first mandate is to find and partner with amazing founders building companies here in NYC. I’m amped to get back into the investment game after a brief hiatus. My second mandate is to help the firm with overall strategy. Over the last decade, I’ve been fortunate to work at some amazing firms and learn from many incredible investors and founders. I’m going to share lessons learned and potentially help operationalize some new programs. The third mandate is to support the existing portfolio with ad hoc executive coaching. I’m currently enrolled in an intensive transformational/executive coaching program, and I look forward to deepening my practice with the Primary family. Finally, I’ll have some freedom, space and time to explore a range of longer-term projects and paths.

Monday is my first day at Primary and I couldn’t be more excited to get started. If you are a founder or operator in NYC and are looking for advice, capital and/or executive coaching, my email is steve@primary.vc. Drop me a note to say hello. I would love to support you on your journey.

Raising money from VCs is an important step in the company building process. It marks the beginning of a long-term relationship that can last longer than a decade. In my experience investing in and advising countless founders, company building is not rainbows, unicorns and lollipops. Startups are filled with adversity, challenge and struggle. That’s why it’s critical to find the right investors who are going to support you when times are good and have your back when the shit hits the fan. It likely will at some point on your journey.

Fundraising should be viewed as a two-way dialogue. Each side should interview the other. While I understand and appreciate the desire and pressure to quickly raise and get back to work, taking enough time to really get to know your partners is a good investment of time and effort. This goes for both sides. If the VC you’re meeting with doesn’t want to spend the time or directly answer your questions, that should be a telling sign. Going into any long-term partnership with eyes wide open is just a smart strategy. Remember, all relationships are complicated. The healthiest ones are built on shared values, open communication and mutual respect. That’s why it’s worth spending the time upfront and understanding who your investors are before they write the check.

So how do you cut through the VCs sales pitch and really get to know the investors during the fundraising process? It starts with asking thoughtful and targeted questions. Be curious. Your objective throughout the process shouldn’t be to interrogate and incriminate but rather to find the right fit and long-term partner(s) for your business. Go for a walk with them. Grab a meal or a coffee. Really get to know them.

If you’re unsure what to ask or what is in bounds, you’re in luck! I’ve created a fairly exhaustive questionnaire that you can reference while you’re on the fundraising trail. Most of the questions are relevant if you’re talking to an institutional VC while some might not be if you’re talking with angels. Know your audience. I recommend doing some research and trying to answer as many as you can before the meeting so you can focus on the most important ones. You won’t have much time so choose carefully.

I hope you find this to be a useful resource before or while you’re on the fundraising trail. Remember, don’t settle or rush the process even if you have ample options. Having the right investor, who is not only a good fit but also will have your back, can be a difference maker. Godspeed!

The Juicy Ones

What makes you uncomfortable about our company? What do you like?

Who in your partnership is going to push back? What are they going to say?

How do we fit your investment thesis and / or align with your worldview?

On a scale from 1–10, how good do you feel about our company right now? Why?

Where are your blind spots with respect to our opportunity?

Can you name a time you stood up for your company in the face of opposition from your partners or other investors?

How have you / the firm handled companies that have underperformed relative to expectations? Can you share some examples?

How would your founders describe you when you weren’t in the room?

Do you engage or disengage when things get difficult?

How do you handle the pressure?

About The Fund

Can you tell me a bit more about Acme Capital and your current fund?

How many partners do you have? Are they generalists or sector-specific experts?

What is your ideal stage?

What is your average check size and do you reserve for follow-on investments?

Do you lead and take board seats?

How does your firm define a “core” investment? Would we fit into that camp?

What are your return expectations?

How large is your current fund and how many more investments do you have left to make?

How does the firm think about bridge rounds or extensions?

Do you have any category or geographic limitations?

What are the last three investments your firm closed and what got you and the partnership excited?

Who are some of your favorite and frequent co-investors?

How can the firm help us build the syndicate for our next round?

The Partner / Investor

What experience or perspectives do you have that are relevant to our company?

What’s your superpower?

What are your core values?

Why did you become an investor?

How many board are you on? How much time do you have for each company on a monthly basis?

Have you ever fired a CEO? What happened?

How long does it take for us to schedule a meeting and / or get on a call?

Do you believe in the partner or the platform?

How would your founders describe you?

What’s your style (hands-on, data-driven, etc.)

What are two or three examples of how you’ve added value to your portfolio in the last month?

Investment Process

Are you running point or will someone else take the baton?

Can you describe your investment process in detail?

Do you have the authority to lead investments or do you work with a partner?

How does the firm make decisions?

How will I know where I am in the process?

On average, how long does the process take from first meeting to close?

Portfolio

What are some lessons you’ve learned from your portfolio that you could apply to our company?

Which companies in your portfolio could we learn from?

Who in founders or operators in your portfolio would be good for us to know?

Do you have any conflicting or tangential companies?

Support

How do you think you could help us?

What’s the firm’s philosophy and strategy on support?

How have you supported companies like ours?

Do I get you and/or the firm? Can you explain?

How do you work with your companies?

Last week, I bumped into a buddy who runs a fairly large venture-backed company. I asked him how things were going. Rather than getting the common response, “everything is great,” he explained that he had spent the last few quarters developing a new product only to discover the customer response has been lukewarm. He said this experience stung because countless hours and hundreds of thousands of dollars were spent building the product. He had also used up significant political capital with his Board. He asked me what I thought. I simply replied, “Don’t let the sunk costs get in the way of deciding what’s best for the business.”

A sunk cost is a cost that has already been incurred and cannot be recovered. We all experience sunk costs in our personal and professional lives. They can include money spent, time, effort and energy. Sunk costs play a big role in startups and investing. Startups and investors are faced with a barrage of sunk costs on a regular basis:

• Spending huge sums of money to develop a product only to discover there isn’t a market for it
• Hiring a key executive only to discover he or she isn’t a fit
• Making a big promotion only to realize the employee isn’t set up for success
• Naming your company and buying a domain only to find another company has the trademark
• Launching a large advertising campaign that doesn’t produce results
• Hiring expensive recruiters or consultants that don’t deliver
• Investing in a company that doesn’t perform relative to expectations

A lesson I learned in school and throughout my career: valuing and harping on sunk costs often leads to poor decisions. It is human nature to try to salvage an investment of time, money, energy and effort. Avoid the trap. They are counterproductive when making forward-looking decisions. They are often an illusion. Don’t let them get in the way. Treat the money, time, energy and effort as gone forever. I realize moving on can be painful and feel barbaric but it can also be liberating.

Whenever sunk costs are influencing decisions, I always recommend coming back to this question: ‘what’s best for the company going forward?’

As an investor, this often presents a dilemma. Investment theory suggests that any incremental dollar invested in a company should be evaluated separately from the initial check. I typically subscribe to this principle. It is sound and responsible. But what happens if a company is in a tight spot and needs additional investment to get to that next critical milestone or achieve an outcome? Is declining an investment in this situation truly in the best interest of the firm? I would argue that most often it’s not.

Venture, especially seed investing, is a human-driven and long-term business. My reputation is all I really have. If I don’t step up in times of need, I’ll eventually develop a bad reputation and founders won’t want to work with me. Being a supporter in tough times is not only the right thing to do from a human and karmic perspective but I also believe it will result in better returns over the long run.

Dealing with sunk costs isn’t so black and white after all. There are grey areas that ultimately challenge our values. If you just focus on what’s best for the company in the long-term you can’t go wrong.