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New to Being Your Own Boss? 5 Tips to Get You on the Right Track

Lisa Dubler

"you got this" written on a board next to a computer

In the era of COVID-19, job seekers around the world are finding new ways to reinvent and reimagine their professional identities to meet the emerging needs of our new normal. For some, this might look like investing in hard skills to support a pivot into a field where jobs are in high demand. For others, this might look like exploring an entrepreneurial track, and perhaps even becoming your own boss. If you’re new to being your own boss, here are five tips to help set you on the right track. 

1. Recognize what motivates you and what holds you back   

As your own boss, the world is your oyster to ideate and create. You have entered into a space where flexibility and opportunity are abundant. But with this freedom comes a great deal of responsibility. You, and only you, are in charge! 

It is up to you to set your goals and priorities, build a client base, craft your messaging, figure out how to be profitable, and much more. While your vision and goals may be very clear, recognizing what motivates you and what holds you back is a critical first step to driving your company in the direction you want it to go. 

2. Set goals with metrics 

Most major decisions in our lives at home and at work are driven by data of some kind. The same can and should be true for your business. Setting key performance indicators (KPIs) can be extremely challenging—especially when you are the one responsible for ensuring that they are met! In the beginning, setting metrics might be driven by what you want to learn, rather than your customer reach or bottom line. 

Feeling stuck on how to get started? Go back to step one and consider your motivations: what is the impact that you want to have? What timeline feels reasonable and realistic? Then, think about what one or two small steps might be to help you move towards those goals. By establishing goals with metrics up front, you will be able to measure your progress over time, in addition to being able to identify patterns of what’s working well and what might need to be adjusted to ensure your future success. 

3. Create a personal advisory board   

If you are new to being your own boss, the first few weeks and even months can feel liberating. There are no required meetings on your calendar from colleagues, no project updates to be shared, and no one holding you accountable for your to-do list, other than yourself. This feeling of liberation, however, can quickly grow into a feeling of isolation, and in a global pandemic, even depression. For this reason, as an entrepreneur—and especially as a solopreneur— creating a personal advisory board is key. 

Your personal advisory board consists of the people who you go to to talk through your challenges and wins. They are the people that believe in you, root for you, and hold you accountable. They may also share in your passions. Most importantly, they are the people who do not shy away from providing direct and insightful feedback. Keep in mind that the people on your personal advisory board do not all need to be people that you have personal relationships with. Some of the most effective advisors for your business can be those you may have never met. If you’re just starting out and want to tap into a powerful (and free!) network of mentors for small businesses, take a look at this great program for small business owners designed by the Small Business Administration. 

4. Design a schedule and stick to it   

Once you have clarity on your motivations and goals and have assembled your personal advisory board, it’s time to design your schedule and stick to it. There is no right or wrong way to go about this. You might want to experiment and perhaps even apply design thinking principles to ideate and test different schedules and see which one lands best. During the ideation process, keep in mind that your schedule as an entrepreneur may look and feel different than it did when you worked for a previous employer. It will also likely include your roles and responsibilities outside of work. Again, there is no right and wrong here. Take advantage of your newfound energy and create a schedule that works for you!

5. Be kind to yourself   

The journey to becoming an entrepreneur requires hard work on multiple levels. You are investing time for introspection to understand your motivations, all while ideating, experimenting, and testing out new structures and schedules to help you achieve your goals. It is not uncommon for entrepreneurs to suffer from burnout, especially within the first year of a new business. You can help yourself thrive by practicing kindness toward yourself. This might look like creating space for self-care, or it might look like saying no to a project that is not aligned with your entrepreneurial goals. The time that you take to rest and recharge, however you choose to do so, will help you show up as your best for yourself and your business. 

Malinda Coler and Laura Schorr contributed insights to this story.

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Are you at a career pivot point and exploring different options, including going to graduate school? If your answer is yes, take a look at the Idealist Grad Schools listings, including details about a virtual career fair, happening soon! 

Lisa Dubler

Lisa Dubler (she/her) is a Career Coach at General Assembly and prior to joining GA, she was part of the Human Resources team at The Washington Post. She began her career in the nonprofit sector, organizing cultural events and community gatherings at Sixth & I. Learn more about Lisa here.

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