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Hey, Colleague: How do I know when it's time to become my own boss?

Hey, Colleague: Practical advice on careers and maintaining a work-life balance.
Since the pandemic, more people are turning their passions and side hustle into full-time gigs.

Send questions about careers, productivity and work-life balance to [email protected]. Please include your name and location, or request to remain anonymous.

Hey, Colleague:

I'm fed up with the 9-5, working for someone else and only being rewarded for doing a good job with more work! I need a change. How do I become my boss? —anonymous

It looks like you are ready to take control of your own life and be your boss. I applaud you for taking the first step: being aware that you are meant for something greater. These mindset shifts in individuals are what powers innovation in our society.

I'm not going to sugarcoat it, but entrepreneurship is not easy, and I want to make sure you know what you're getting into. Entrepreneurship is constant problem solving and requires ruthless resilience. Most entrepreneurs are hard on themselves because of their drive to succeed and to produce exceptional results. Some days you will feel like a failure if you don't achieve your goals, and other days you will be riding off a high after signing on a new client. 

Entrepreneurship is a lonely roller coaster, so you need to ask yourself: "am I ready for the ride?"

Here are some traits needed to become a successful entrepreneur:

  • Adaptability and ability to pivot fast. Entrepreneurship is unpredictable.
  • Intrinsically-motivated self-starter. No one is your boss telling you what to do, so you must have the discipline to stay focused while creating your structure. 
  • A die-hard work ethic, which also requires intense passion. If you're not passionate about your business, it will be challenging to follow through when times get tough.
  • Ability to take risks and not be afraid of failure. You may fail over and over but reframe each failure as a "lesson," try not to make a mistake twice. Pick yourself up and try again.
  • Relentless curiosity and eagerness to learn. Wanting to see and understand different perspectives will make you a well-rounded, creative entrepreneur and allow you to develop varying solutions to your problems.
  • Be emotionally-intelligent. Emotional intelligence is the ability to manage our own emotions while recognizing and understanding others'. To be a team player and build strong relationships with your clients, team, and stakeholders, you must understand that emotions can drive our behaviour and impact others. A good leader will use emotional information to guide thinking, make decisions and make adjustments while adapting to diverse environments. This prevents impulsive behaviour and rash decisions while increasing empathy, improving social awareness, relationships and self-esteem.
  • Be goal-oriented. To be successful, entrepreneurs must have a strong vision of what they want and stay the course. They must always have their eye on the bigger picture while at the same time being able to focus on the steps needed to get there.
  • Be an effective communicator and have the ability to sell. We are constantly selling something, including our brand or a business idea, to investors or potential hirees to make them want to work for you (unmotivated employees will often come with lousy results).
  • Stay humble and maintain a positive attitude. This includes owning up to your mistakes when you are at fault.

Does this sound like you? If you have some of those traits—but not all, don't fret. The entrepreneurial process is also a journey to learn, build, test, fail and repeat. 

If you are not ready to go all-in, have you thought of starting a side hustle? Small businesses are booming, and the cry to buy small and buy local is thundering. You don't necessarily need to quit your day job before diving in. It's never a bad idea to test the waters.

How to be your boss:

  • Figure out what you are passionate about. What do you like to do in your free time? What are your hobbies? What conversations light you up? What did you want to be when you were growing up? What do your friends say about you? Those are all excellent questions to start asking yourself to find your passions.
  • Make sure your product and service are solving a problem. To live a happy and meaningful life, you must be kind, give back, and help others. Human beings are social creatures, and it is in our blood to help, so not only will you be creating a fulfilling life for yourself, you have a product and service that people need.
  • Get inspired. Go on social media, Etsy, Fivver or similar sites to get inspiration from what others are making or selling. Make vision boards. Go for walks, exercise or meditate to clear your mind to find clarity.
  • Connect with other entrepreneurs. Many active Facebook groups and associations (such as the Small Business Owners of BC) offer support, tips, and recommendations. I am part of a few, and I've gotten so much value— from hiring contractors, recommendations, book-keeping tips, marketing, etc. Don't be afraid to ask because people love to share and help. You must understand what it takes to start your own business. 
  • Hire a coach. Learning from someone who has already done it will be your best investment and save you a lot of time navigating the basics.
  • Start now. If you don't, you will wish you had started soon, a year from now. It's never too late to start exploring your passions.

Benefits of being your boss:

Being your boss meets our basic psychological needs of increasing overall well-being and self-determination. Based on the self-determination theory, four factors influence meaningfulness: autonomy (freewill; the desire to feel in control of one's life), competence (desire to gain mastery and be able to control the outcome) and relatedness (desire to connect and relate to others).

Secondly, you will have time freedom, which was a reason that drove me to leave a stable and lucrative decade-long career at 27. I value my time immensely because money can always be made, but you will never get time back. 

The urge for new challenges and a change in environment was another important reason I wanted to change careers. I felt I couldn't move up in the company, and the options didn't align with my passions and values. As I got older, I learned my true passions, and I had to make tough decisions to pivot directions. I also understood that I needed to expose myself to as many experiences as possible to grow.

So are you ready to leap? I always preach: if something excites you but scares you at the same time, it's always worth exploring. Remember, nothing good ever grows in the comfort zone—and you will have a whole community of entrepreneurs at your back helping you along the way.

Kate Pn writes about mastering a healthy work-life balance by focusing on productivity hacking. Write to her at [email protected].