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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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Last Updated on January 14, 2019

The Key to Finding Job Satisfaction and Having a Successful Career

The Key to Finding Job Satisfaction and Having a Successful Career

Regardless of whether you hold an entry-level administration role or regularly travel to the ends of the Earth as a hot-shot senior executive, you can still find yourself harboring an emptiness… a feeling that something is missing. A popular assumption that experiencing job satisfaction and a successful career should be underpinned by a well-rounded suite of tangible benefits, no longer holds true for many of us.

We’d never deny health care benefits, appropriate and fair remuneration, bonuses and travel perks in a job package. However, even if served to us on a silver platter, those features can only satiate us to a certain point.

You might wonder what governs entrepreneurs and start-up business owners to quit their lucrative jobs, essentially look the gift horse in the mouth and kiss such benefits goodbye! There can be an irresistible pull to mastermind a business with products and/or services that serve the greater good of community wider than that constituting their daily existence.

Even with research showing entrepreneurship to pose greater threats to their mental and physical health, this unique breed of individuals choose to go against the grain in chasing their dreams of being their own boss. Why? Why would anyone risk this type of career suicide?

Whether you’re an employee, have recently taken the leap to being a business owner or been in business for a while, the commonality is a congenital condition we all share as human beings; to feel a sense of purpose, value and contribution to our community. Despite it being harder to find this for ourselves in today’s world, these approaches will help you achieve ultimate satisfaction through the twists, turns and joyrides that are essential features of shaping a successful career.

1. Search for Opportunities That Feed Your Passion, Not Temporary Excitement

Even though well-intended, the ‘feel good now’ compass that career coaches and consultants often recommend you use to create career satisfaction can actually do you more harm than good. Excitement is transient. It doesn’t last. Passion is the compass you need.

Passion and excitement are two different things. The resounding career legacy that still draws you to turn up on the job regardless of the sunshine or storm that awaits you…that’s passion. It’s like a mental and/or emotional itch you can’t shrug off. Staying attuned to that calling will breed success for you sooner or later. Patience is key.

You’re also likely to have more than one key passion. Beware of getting caught in the notion you have to find your one true purpose. In fact, run immediately from any coach who tells you there is only one. There isn’t.

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Your passion is a journey that can take multiple forms so forget thinking there is the single dream job out there that will give you satisfaction in every way you can imagine. It simply doesn’t exist.

Consider embracing different roles and projects to help you fuel your passion or fuel your pursuits in finding it. Job satisfaction and your career success will be all the more sweeter from a wider range of enriching experiences.

2. Don’t Position Job and Career Satisfaction Assessments as Pivotal Guides to Your Success

Despite their popular use for vocational guidance, assessment tools such as Gallup’s Clifton Strengths and the Myers Briggs Type Indicator have come under fire[1] as being limited to the amount of true value and direction they can offer partakers.[2] These and many other guidance assessment tools (e.g. VIA Character Strengths , DISC ) are self-report questionnaires that don’t have normative population data against which to compare your results.

Simply remember these tools help you develop a stronger sense of what you identify as strengths and weaknesses within yourself, not in comparison with other people. They will still add insight around what sorts of career opportunities, tasks and projects are going to light your fire, what ones are going to extinguish it and what will prod and keep the coals steadily smoldering.

3. Be Clear on Your Personal Values, Ethics and Principles and Choose Relationships That Support You Honoring Them

Teamwork, collaboration, open communication and trust are commonplace for any flourishing work environment. However, whether or not your personal values can be honored in your work can make or break your job satisfaction.

How committed do you want to be to an organization that expects an average of 10 unpaid overtime hours every week under the guise of ‘reasonable overtime’? Are you willing to accept their construing this expectation as ‘strong commitment’ at the expense of your partner and children waiting at home for you? What are your boundaries concerning when you clock on to their time and when you clock off to yours?

Being very in tune with what your personal values, principles and ethics are will bid you well in the job satisfaction stakes. Spending time to reflect on experiences and working relationships you’ve had – the good, the bad and the ugly – will help you make well-informed searches and grounded decisions that will propel your career success.

Finding and nurturing relationships with associates and colleagues who share similar values doesn’t just make your day-to-day pursuits more enjoyable. You become fortunate to work with like-minded people who will support, understand and appreciate you like a second family.

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Being able to honor your personal values in your work means you will still be able to sleep at night when you have to tread where others fear to, and make extremely difficult decisions others would never ever dream of having to make as you forge success in your career.

4. Be Clear on Your Own Definition of What Having a Successful Career Means for You

It’s tempting to get caught up in the ideals and projections of success expressed by those we love, admire and respect. Underneath, we all want on some level to belong to a successful club of some sort.

With research reporting how much money we feel we need to be truly happy,[3] many of us try to subscribe to the notion that having the car of our dreams or taking a European holiday annually will not bring us happiness. The truth, however, for many of us is these tangible rewards are congratulatory reminders of our persistent efforts to chase our career pursuits.

If those are things you aspire to, don’t let anyone steal your desire and want to feel deserving of these things, that those are some parameters by which you define your career success.

Despite consistently being the top revenue earner for two years running, you may not wish to become the sales manager. You may not wish to step out into running your own business even though you consistently excel as an employee, delighting clients and repeatedly receiving glowing testimonials.

Your definition of career success might be enjoying the predictability of a regular workplace routine. You get to leave – without feeling guilty – at the same time each day, love the people you work with and get to spend a good, uninterrupted amount of work-stress free quality time with your family. That picture is also blissful job satisfaction and complete career success.

5. Identify the Sorts of Challenges and Problems You Want to Learn to Overcome

Standard advice you might receive from a career coach might be to look for opportunities where you get to capitalize on exercising your strengths and career-related activities you enjoy.

However, to become a success at anything involves improvement. To excel at anything often involves stepping outside boundaries and comfort zones where others wouldn’t. This means dedicating focus and attention to things you’re not so good at and things you don’t like.

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Here’s where working with a coach can be particularly helpful. Map out the experiences that were unsavory in your working history. Were there challenges you opted out of, projects you failed at or toxic relationships that blasted your sense of purpose and self-worth into oblivion? It’s within these experiences that you might just find the most valuable lessons and guiding lights for your trajectory to achieve greater job satisfaction.

If your natural leadership style is to be a collaborator, finding opportunities that require you to apply a more dictatorial style might be needed. Discussing a secondment or short-term project where you get to develop and test your skills can be a step further in earning contention to lead a larger project down the track.

With several of the company’s boldest personality types penciled to roll out the operation, you’ll not only develop skills that earn your right to throw your hat in the ring; those key players have an opportunity to see your competence. You can then work on building relationships with those stakeholders before you need to hit the ground running should you win the lead.

Greater job satisfaction comes with planning and choosing the lessons and opportunities you want to learn, not desperately flailing, floundering and hoping for the best.

6. Keep Reviewing Your Goal Posts and Be Amenable to Change

The word ‘career’ is indicative of a longer-term pathway of change, growth and development. The journey is dynamic.

You will accumulate new skills and let those you no longer need, become rusty. Your intrigue will be stimulated by new experiences, knowledge and people you meet. Your thinking will continue to expand, not shrink. As a result, your goalposts are likely to change.

A major part of enjoying a successful career is not just setting goals effectively, but regularly reviewing and readjusting them where necessary. However, moving the posts or the target still needs to take place by applying the same processes by which you originally created them. The strength of your emotional connection to those revised goals needs to be the same, if not stronger.

By asking yourself the following questions, you can assure your developmental and growth trajectory is still on course:

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  • Would working toward these goals still allow me to honor my personal values, principles and ethics at the same capacity if not greater?
  • Do the activities I need to undertake to meet these goals honor my highest priorities?
  • Does this feel right for me and those who are nearest and dearest to me?
  • Is this aligned with my passion?
  • Is chasing this goal a right step for me to take now or is this a detour or distraction which could delay my greater plan?

Each of your career goals should have different review periods. Whatever you do, stick to the review schedule you set. It will not only keep you focused but help you see your progress (or lack thereof) and allow you to timely re-chart your course before you get too far down the track. You don’t want to waste time haphazardly heading in the wrong direction.

7. Be Prepared to Let Go

It can be unfathomable to us as to why others risk leaping into the unknown when everything truly appears fine and dandy in the career realm. The company provided stability, recognition, financial success, interesting projects and the promise of a promotion…what was wrong? Why now jump sideways to run a café or train in another field altogether?

Nothing may have been wrong at all. It was all going right. It was just the end of a chapter. Perhaps the yearning for the next step is actually taking a different trajectory entirely. You may want to simply experience a different rhythm. Perhaps it’s time to pursue a different passion.

If you have leaped from employee-land to freelancing or have made the reverse-jump (or you know someone who has), you will have quickly grown a different appreciation for pros and cons each work lifestyle brings. Working for yourself can bring the greater realization of your creativity, whether or not it can be monetized to earn you a living.

When your customers are buying you or a product you designed and fashioned, there is a direct level of appreciation and gratitude that can elevate your confidence in the way you have never experienced as an employee, regardless of your rank.

Similarly, there are times where we need to recognize our business ventures were adventures, not long-term life-changing empires. There are times we need to recognize that time is what provides the clearest limitation of how long we persist for in such pursuits.

We have to recognize the absence of enough financial, mental, emotional and physical breadcrumbs that tells us we’re no longer meant to push in that direction. At least, not for the present time.

The Bottom Line

Above all, keep the momentum. As long as you remain committed to pursuing work opportunities that allow you to honor your highest priorities, the truth of who you are and what you stand for, achieving ultimate job satisfaction and a successful career will never be too far away.

More Resources to Help Advance Your Career

Featured photo credit: Csaba Balazs via unsplash.com

Reference

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