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6 Tips For Navigating Your Role As An Entrepreneur

6 Tips For Navigating Your Role As An Entrepreneur

On August 17 I went to the YC Alumni demo day in Mountain View. As the class of Summer 2015 proudly pitched their ideas in perfectly rehearsed two and half minute pitches, my multitasking mind thought about how much time has passed since Vasco Pedro, my fellow co-founder and CEO, presented Unbabel on that same stage in March 2014. It felt like eternity. I began to think further back to my first startup, a total disaster that left me penniless in 2012, then to when I quit my job to start a female beauty company that never made off the paper, and to my first job in tech in 2005. It’s been 10 years since I embarked on my journey in this crazy world of startups, technology, subscriptions, and hyper growth, and became an entrepreneur.

Being an entrepreneur is a difficult job that we’ve all chosen for different reasons, but the underlying motivation is our passion for ideas that we believe in so much that we’re willing to do what it takes to make them come to life. After having worked with startups around the world, I’ve gathered enough experience to last me a lifetime. Here are my top six tips for navigating your role as an entrepreneur.

Know your self worth

It’s easy to confuse your self worth with the growth rate of your company, how much money you raised, or how many times you heard the word “no” this week. After co-founding ActualSun, the team imploded and we failed to build a product, lost our pilot customer, and the trust of our investors. I thought I failed as a manager and as a person. Looking back I realize it was just a bruised ego and allowing myself to think that way only made it harder to get back on the horse and try again. Building a company is a 24/7 job and it’s natural to obsess about what’s going on with your startup. Thoughts are constantly swirling through your head about how to grow, who your customers are, how to sell, who to sell too, how your ideas stand out, and how to communicate them in a meaningful way. When you spend so much time thinking about something, you begin to identify personally with it. It stops being your company and starts being you.

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But it’s not. You’re a worthy, unique, valuable human being just because you are you. There is no point in identifying yourself too much with your failures or successes. If you get down when the business is down, it’s much harder to turn it around and you might fail to see the window that opens when that door is slammed in your face. Balancing your reactions to the ups and downs of your business is all about remaining confident in the face of failure and maintaining modesty in your success.

Keep calm and try again

If you ever met me in person you’ll see “Keep Calm and Try Again” is actually my phone’s screensaver. As entrepreneurs we naturally see ourselves as leaders and are always striving to succeed. Our desire to be the best often causes us to go into a bit of a panic when things don’t work out the way we had hoped. A large majority of the things we work on will fail and on multiple levels; weer that’s your campaigns, channels, customers you go after, or people you hire. You will make mistakes and lots of them, but that just means you’re making decisions and taking chances.

In a way, it’s like A/B testing everything. I first started getting used to trying things when I worked for TIMWE. We did a lot of online ads, and had tons of different landing pages. We would test if a particular piece of content would sell, a new affiliate network, or a new banner design. It sounds basic, but this was in 2006 before Unbounce and Optimizely made it easy, we were running these experiments manually. The marketing team discussed our experiments as a group on Monday mornings and if it worked we’d do more, if not, we’d try something else. You can apply that to literally everything! Remember, each attempt is a learning opportunity, a teachable moment. The silver lining of any failure, is what you learn as a result. A friend of mine summarized it perfectly by saying, “Learning is what you get when you don’t get what you want.” I love that sentence and always look for what I learned in each project. If you can take your failure and turn it into an opportunity for growth, you and your company will be able to turn failures into success.

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Become a well rounded person

Even though you might feel like you don’t have enough hours in the day, taking time away from work to hone different interests, hobbies, and passions is good for business. Aside from it being a good stress release, it makes you a richer and more well-rounded person and opens you up to meeting people with different opinions, skills, and experiences than you. All my YC batch mates (Go Winter 14!) have some kind of interest that helps take their mind off work and do things with different people. They participate in a range of activities from stand up comedy, paragliding, and team sports, to climbing mountains, camping, building cities in the desert, and cooking. And me? I did my first triathlon on August 23!

The beauty of adding more dimensions to your life is that it will actually make you a better founder. Here’s a secret, as an entrepreneur you’re always selling the vision, the technology, the company, to investors, customers, employees, family, and friends. Selling is all you do, and it’s much easier to sell if you can create rapport with people around other things you might have in common aside from your company.

Remember you’re not alone

I hear these phrases time and again, “most startups are shit-shows”, “there is always something broken”, “the problems are just different when you grow”, “as a CEO I focus on the part of the company that is under performing the most and fix it.” Every step of the way, from idea to IPO, hell is always about to break loose and something that might kill your company is always about to happen. Not only do we all have some type of problem to solve, we all think we’re the only ones. We’re not, everyone goes through the struggles of building their business.

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I have a group of startup friends I have dinner with once a month just to talk about the companies we are building in a friendly supportive environment (with good food and wine). Find your peers, start a group, get together regularly, and talk it out. Just sharing dilemmas out loud is often half the solution, and as an added bonus, you say them to a room full of other entrepreneurs who can draw on their experiences and offer advice.

Practice your people skills

Dealing with other people is hard, and it’s crucial that you learn to be great at it. Find ways to make people do what you want even when you don’t have hierarchical power over them. No, I don’t mean be manipulative. What I mean is, make people want to work for you. Learn what interests the people you work with, how they want to expand their skill sets, and how you can help them. Knowing these are critical for a successful business.

There’s a new contract between companies and people. In the old days people were resources who gave themselves to companies in exchange for predictability, security, and a job for life. Today, that type of employment is a distant memory. There’s no predictability anymore, so instead of searching for jobs that can provide security, people want jobs that offer them the opportunity to learn, better themselves, and work in a variety of capacities. It’s your job to create those opportunities for them and to make sure your team is naturally aligned with where you’re going and want to be with you for the ride.

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Respect your co-founders

The way you communicate with your co-founders sets the tone for your whole company. You and your team of founders are the backbone of your startup and set the company-wide example of how to be team players. When business gets stressful, your co-founders are your support system and are just as invested in the success of the company as you are. Always assume they are doing the best they can and working as hard as they can. You didn’t choose each other randomly, it was a conscious choice to go into business with one another and when times get tough, it’s important to remember that they are invested and deserve your respect.

It’s equally important to never let doubts or unspoken pain fester. Everyone is human and falls prey to outbursts that come across as disrespectful. At Unbabel we call that emotional debt, and unlike technical or sales debt, this isn’t the kind of debt that you can afford to pay back later. A startup is like a relationship and when doubts and resentment begin to build up, they are bound to surface in the throes of another issue. So don’t let it build up and have the tough conversations about your stress, fears, and needs, and listen to those of your founders and your team. Make sure to find ways to make everyone feel valued and part of the team. As a way to avoid a build-up of emotional debt, take company trips and do something fun to build a strong connection between each member of the team.

These tips are helpful for every entrepreneur who wants to navigate successfully through the minefield of living the startup life. Implementing these key strategies will help you develop yourself personally by having a grounded sense of yourself and becoming more well-rounded and empathetic. You’ll grow your business by remaining calm in the face of failure and looking for the next opportunities. Finally, you’ll be better equipped to nurture your team by removing emotional debt and promoting an environment of mutual respect. If all else fails, listen to your gut and remember that you catch more flies with honey than you do with vinegar.

Featured photo credit: Navigator/ Thomas Abbs via flickr.com

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Published on March 26, 2019

How to Write a Cover Letter for a Career Change (Step-By-Step Guide)

How to Write a Cover Letter for a Career Change (Step-By-Step Guide)

Embarking on a career change, tiny or big, can be paralyzing. Regardless of the reason for your desired career change, you need to be very clear on ‘why’ you are making a change. This is essential because you need to have clarity and be confident in your career direction in order to convince employers why you are best suited for the new role or industry.

A well crafted career change cover letter can set the tone and highlight your professional aspirations by showcasing your personal story.

1. Know Your ‘Why’

Career changes can feel daunting, but it doesn’t have to be. You can take control and change careers successfully by doing research and making informed decisions.

Getting to know people, jobs, and industries through informational interviews is one of the best ways to do this.[1] Investing time to gather information from multiple sources will alleviate some fears for you to actually take action and make a change.

Here are some questions to help you refine your ‘why’, seek clarity, and better explain your career change:

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  • What makes me content?
  • How do I want work to impact my life?
  • What’s most important to me right now?
  • How committed am I to make a career change?
  • What do I need more of to feel satisfied at work?
  • What do I like to do so much that I lose track of time?
  • How can I start to explore my career change options?
  • What do I dislike about my current role or work environment?

2. Introduction: Why Are You Writing This Cover Letter?

Make this section concise. Cite the role that you are applying for and include other relevant information such as the posting number, where you saw the posting, the company name, and who referred you to the role, if applicable.

Sample:

I am applying for the role of Client Engagement Manager posted on . Please find attached relevant career experiences on my resume.

3. Convince the Employer: Why Are You the Best Candidate for the Role?

Persuade the employer that you are the best person for the role. Use this section to show that you: have read the job posting, understand how your skills contribute to the needs of the company, and can address the challenges of the company.

Tell your personal story and make it easy for hiring managers to understand the logic behind your career change. Clearly explaining the reason for your career change will show how thoughtful and informed your decision-making process is of your own transition.

Be Honest

Explain why you are making a career change. This is where you will spend the bulk of your time crafting a clear message.

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Speak to the mismatch that may be perceived by hiring managers, between the experience shown on your resume and the job posting, to show why your unique strengths make you more qualified than other candidates.

Address any career gaps on our resume. What did you do or learn during those periods that would be an asset to the role and company?

Sample:

I have been a high school English and Drama educator for over 7 years. In efforts to develop my career in a new direction, I have invested more time outside the classroom to increase community engagement by building a strong network of relationships to support school programs. This includes managing multiple stakeholder interests including local businesses, vendors, students, parents, colleagues, the Board, and the school administration.

Highlight Relevant Accomplishment

Instead of repeating what’s on your resume, let your personality shine. What makes you unique? What are your strengths and personal characteristics that make you suited for the job?

Sample:

As a joyful theater production manager, I am known to be an incredible collaborator. My work with theater companies have taught me the ability to work with diverse groups of people. The theater environment calls for everyone involved to cooperate and ensure a successful production. This means I often need to creatively and quickly think on my feet, and use a bit of humour to move things forward to meet tight timelines.

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Feature Your Transferable Skills

Tap into your self-awareness to capture your current skills.[2]

Be specific and show how your existing skills are relevant to the new role. Review the job posting and use industry specific language so that the hiring manager can easily make the connection between your skills and the skills that they need.

Sample:

As the first point of contact for students, parents, and many community stakeholders, I am able to quickly resolve problems in a timely and diplomatic manner. My problem solving aptitude and strong negotiation skills will be effective to address customer issues effectively. This combined with my planning, organization, communication, and multitasking skills makes me uniquely qualified for the role of Client Engagement Manager to ensure that customers maintain a positive view of .

4. Final Pitch and Call-To-Action: Why Do You Want to Work for This Company?

Here’s your last chance to show what you have to offer! Why does this opportunity and company excite you? Show what value you’ll add to the company.

Remember to include a call-to-action since the whole point of this letter is to get you an interview!

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Sample:

_________ is a global leader in providing management solutions to diverse clients. I look forward to an opportunity to discuss how my skills and successful experience managing multiple stakeholders can help build and retain strong customer relationships as the Client Engagement Manager.

Summing It Up

Remember these core cover letter tips to help you effectively showcase your personal brand:

  • Keep your writing clear and concise. You have one page to express yourself so make every word count.
  • Do your research to determine ‘who’ will be reading your letter. Understanding your audience will help you better persuade them that you are best suited for the role.
  • Tailor your cover for each job posting by including the hiring manager’s name, and the company name and address. Make it easy on yourself and create your own cover letter template. Highlight or alter the font color of all the spots that need to be changed so that you can easily tailor it for the next job application.
  • Get someone else to review your cover letter. At a minimum, have someone proofread it for grammar and spelling errors. Ideally, have someone who is well informed about the industry or with hiring experience to provide you with insights so that you can fine-tune your career change cover letter.

Check out these Killer Cover Letter Samples that got folks interviews!

It is very important that you clarify why you are changing careers. Your career exploration can take many forms so setting the foundation by knowing ‘why’ not only helps you develop a well thought out career change cover letter, [3] but can also help you create an elevator pitch, build relationships, tweak your LinkedIn profile and during interviews.

Remember to focus on your transferable skills and use your collective work experience to show how your accomplishments are relevant to the new role. Use the cover letter to align your abilities with the needs of the employer as your resume will likely not provide the essential context of your career change.

Ensure that your final pitch is concise and that your call-to action is strong. Don’t be afraid to ask for an interview or to meet the hiring manager in-person!

More Resources About Career Change

Featured photo credit: Christin Hume via unsplash.com

Reference

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