I’ve experienced more in the past 2-3 years in regards to business and life than I probably have in my entire 25 years. Switching from medicine to tech, becoming a software engineer having never written code, moving across the country alone, leaving bigwig corporate to do my own consulting for startups, and taking startups from 0 to over a million user reach. These formative, whirlwind years helped me to grow immensely and calibrate how I choose to interact with the world to optimize business relationships, career, and success.
In this time, I’ve kept track of the lesson nuggets that represent pivotal realizations learned from failures and I regularly read back through them to guide decisions and actions. I’m constantly adding to this list unique lessons that come from trial and error moments (startlingly common), here’s what lives today.
Keep in mind, these are career-focused. I’ve also learned a number of lessons about life, personal relationships, mindfulness, health, and happiness but that’s not what this post is for. Career isn’t everything but being the productivity-obsessed and independently-employed human I am, it tends to intertwine with my personal life in more ways than one. I like it that way.
Write and speak with conviction, simplicity, and clarity. No one’s giving you points for saying “ameliorate” instead of “improve”. Hemingway is a legend for a reason.
Embrace big vision. Thinking big is the first step in executing big.
Take initially uncomfortable calls, meetings, networking events and go into them ripe with confidence and enthusiasm. I’m almost always happy I did, everyone has something to teach you.
Be confident in your abilities and experience. People don’t doubt you until you doubt you. You get to where you want to be by acting like you’re well equipped to be there and like you’re one of the best people to be there. You must be your own advocate.
Initiate, do, act before being asked or instructed. Startups are often lacking in direction and structure, be a self starter that contributes value by default. It’s overhead for any manager/leader to incessantly assign explicit work, be someone who does the work without needing that, but be sure it’s the RIGHT work (read Effective Executive by Peter Drucker).
Have strong opinions, loosely held. Be open to other ideas and insights, that’s how you learn and that’s how the best results arise—synergy across many minds working in tandem with one another.
Speak with the 'Yes, and’ approach. Collaborative, open, and explorative. Not argumentative, rigid, or arrogant.
Do it now. Don’t push it to later. It doesn’t always need to be a scheduled meeting, if a topic comes up that can be addressed now then address it now.
Don’t accept money or gifts if you can help it. Pay for the coffee, the lunch, the drink. There’s no such thing as a free lunch, and the simple act is remembered.
Launch the point of the meeting sooner. Meetings can be bottlenecks on their own, don’t make them time eaters more than they need to be. State the goal, accomplish the goal, summarize a recap/action items, finito.
Define successful processes and repeatedly apply them. Test processes until you find one that works then apply it again and again.
Be thankful for what you have and nourish it. Don’t assume the comfortable and nice will stay there whilst you look for something better.
Go for the top. Don’t accept a no from someone who can’t tell you yes.
Don’t be frustrated or ashamed with being an underdog. Everything starts somewhere. If you want to be somewhere where you can make an impact, you have to do just that—make an impact, be a driver in the success, prove your worth with execution and results.
Let others finish speaking. And deeply listen. Don’t just think about what you'll say next. Don’t interrupt. Let people finish their thought, their sentence, their input before jumping in.
Be Nice. People work with people they want to work with. Surround yourself with successful, smart people and make them want to work with you by being kind and giving and respectful.
Think for yourself and construct your own beliefs and values, speak to them with confident conviction. Don’t constantly feel the need to cite a book or podcast for credibility or argument sake. Think for yourself, have your own truths and beliefs and back them with a sound argument that you yourself constructed, confidently.
Take others’ words with a grain of salt, don't immediately see them as truth. Internalize them as insight that you deconstruct for your own purpose, think about what it truly means and how it applies (if it applies) to your own life.
Stop skimming. A wealth of information creates a poverty of attention.
Don’t ever take business personally.
Go first. Introduce yourself first, smile first, call first.
Be decisive.
Don’t ask a question just to ask a question. Do it because you really want to know something, and make that known, follow it up, continue the conversation upon the answer. Be interested and curious and humble and open. The wise man once said nothing, if you don’t have an output-driven question, shut it.
Have a clear, defined proposal for what you can do for someone or a company when you meet with them. Don’t expect them to come to you with a proposal, you know your contribution and skills more than anyone. Plus, you know what you want to do, so own that, set the stage.
Just relax, everyone’s a human just trying to get by too. Be candid and transparent and genuine as much as the situation allows.
Step up when the leader doesn’t show. The people that are there were expecting a leader, they were prepared to be led, now they don’t have that. If you step in and do so, it's a relief to all and you get a free opportunity to flex those skills.
Be humble and embrace sacrificing what you are for what you want to become. In the beginning, you don’t have credential or experience leverage in your career. Be open to doing things for others for free and embracing the opportunity to learn and prove your capabilities.
Have a few key questions that are deep and thought-provoking that you ask others consistently. This helps you find patterns in answers. It also launches meaningful conversation vs. small talk networking. It’s memorable, people remember how you made them feel not what you said.
Treat clarity and transparency as prereqs. This is vital for doing business. Before agreeing to partnerships, make sure I’m on the same page with the partner as to their expectations, where they are currently, and their plan for the future. This mitigates discovering gaps and misalignment at a point when you’ve already invested time and resources to the partnership.
Speak ill of no one. Gossiping is so many things–none of which are useful, effective, or positive.
Develop ubiquitous language, consistent communication. Use a naming convention for product lines and business efforts. Most people are scared to ask if they don’t know what something is, thinking they’re supposed to. That’s inefficient and wastes time.
Zero bullshitting. Don’t sugarcoat out of weakness or hesitance.
Take ownership.