How to Move Gracefully from Employee to Boss

Leaders of organizations, businesses and non-profits likely didn’t start at the top. There was a point when that leader ceased being an employee and became in charge of the entity and/or staff. Training, books, and mentors can teach you best practices as you transition from employee to boss. Unfortunately, we don’t do enough to help employees become ready for leadership positions.  

The journey from employee to the boss is not a linear one. Social entrepreneurs who are starting or running a business or nonprofit organization will make this transition. Transitioning from employee to boss is not easy whether you are starting something new or inheriting someone else’s legacy.

When I’m coaching women of color, I often find myself explaining how this mindset shift from employee to boss is one of the things that is holding them back from making an impact. It is difficult for “helpers” who have worked for organizations their entire career. Founders must transition into being in charge of their own mission and vision. 

If you are currently leading a social business or nonprofit, take a moment to remember when you told yourself “holy shit! I’m in charge of this thing!” For people starting out, your version might be “holy shit, I need to build this thing!”

Moving gracefully through this transition and mindset shift is necessary if we want to lead change efforts. Shifting your mindset from employee to boss is especially important if you are the founder of a social impact organization. 

What Happens When You Stop Feeling Fulfilled? 

In the post-pandemic world, many people have found it difficult to stay in a job they do not find fulfilling. One lesson many of us learned is that there is too little time to be unhappy every day simply for a paycheck. 

In the book, Sister Armor, I share the very moment when I decided to go from employee to boss. The story starts with the only time in my career when I lost my job and found myself without a paycheck.

I realized “life is too short to do something every day that you don’t love. Each of us has a gift, a set of talents that have the potential to change everything for someone else. 

When we work in environments where our gifts are not welcomed, where our talents are not harnessed, and our skills are not honed, we slowly wilt and die. We die in our chairs with bad posture and hip problems wondering where our adulthood led us wrong. Unhappy that we spent so many years of our beautiful energy working in a manner that didn’t suit us for someone else’s mission that didn’t serve us.” 

When you are unfulfilled in your current jobs and capacity, you are less likely to be effective at what you are doing. You risk burning yourself out and stifling your progress as a professional and a person. You also risk hitting a ceiling where you can’t progress any further. 

If that sounds familiar, read on. Here’s your easy guide to how you can mentally break free from your current situation and become your own boss. 

Lesson #1: Ask Yourself ‘Is The Grass REALLY Greener?’ When You Move From Employee to Boss 

The alternative to working for someone else is becoming your own boss. That means all the good and bad things that go with it. Being your own boss sounds legit like the best thing ever. 

That’s until you realize that everything is dependent on you being successful. Choosing to be your own boss comes with a lot of mindset garbage around the pressure to succeed. 

If you are thinking of making the leap from employee to boss sit down with yourself. You need to make sure that you are mentally strong enough to withstand the challenges ahead. Weighing the pros and cons can help you determine if the grass really is greener on the boss or the employee side.

For many people who choose to be their own boss, the grass really is greener. It’s about mental health. When you are unfulfilled and burned out, your mental health suffers. The uncertainty of self-employment can weigh heavy on your mental health as well. However, it’s more important to be able to control the environment and how you do business. You can create a business that is supportive of your mental health and personal development.

Lesson #2: Get Comfortable With The Uncomfortable

The ups and downs of entrepreneurship are daily and plentiful. There’s nothing comfortable about being self-employed. The roller-coaster ride includes who you choose to do business with and how you spend your time and money. 

When you decide to be your own boss recognize that there are highs, lows, and everything in between ahead. One of your many jobs is to persevere and keep your eye the prize. You have to fight for what you want as you transform from your old employee-self to your new badass boss-self. 

Self-employment can be difficult and rewarding. You have the potential to make as much money and impact as you want. You also have the potential to fail. 

Are you trying to decide whether becoming your own boss is worth it? Many business leaders recommend having at least one year’s average of your salary available before you venture into full-time self-employment. Even more astonishing is that many millionaires have at least 7 streams of income. 

The financial barriers alone are usually scary enough for people not to pursue going out on their own and choosing to remain an employee forever. The thought of having to pay for your own health insurance or rely solely on your own ability to raise capital or get sales is daunting for many people. (Including me! I’m not immune to this fear BTW. I’ve just chosen my mental health instead of being afraid.)

Usually, entrepreneurs who are soul-guided or heart-centered aren’t trying to become millionaires by helping others. Instead, they are usually driven by the prospect of making millions of dollars in profit or donations so they can help more people. 

Entrepreneurship lacks security, that’s what makes it so sexy to some people. Risk and reward require you to believe in yourself wholely and that can be tough for some people to do. If you’re going to be successful and make an impact as your own boss, you can’t expect self-doubt to contribute to your efforts.

You can only get to your goal if you don’t tap out too soon. When you’re the boss you get to say when to tap out or when to go hard.

Lesson #3- Being the Bosss Lets me Help Who I Want To Help How I Want 

Many people who are “helpers” want to help as many people as possible. You might be saying to yourself “I want to be my own boss so I can reach more people.” 

The other benefit to social entrepreneurship is you get to use your knowledge to do good and help others. As your own boss, you can use your knowledge and take initiative to make the world a better place. You can also learn the things you need to be successful, get mentorship, and leverage support like coaching.

When you’re in charge of how your social business or nonprofit is run and structured. You get to decide how you offer support and to who you offer support. You also get to figure out how to fund it all, so there is a downside of course. 

This was one of the most exciting parts about being my own boss. As a coach for Latina entrepreneurs, I built my business off the premise that I will be making an impact in the Latino community. I help build capacity for this and the next generation of leaders to show up and fulfill their life’s purpose. 

This is an important part of my business and I could not fulfill this mission while I was employed by the government. In my prior roles, I felt restricted because I was told who I could help and how to help them. Now as my own boss, I can decide that my business has whatever impact mission I want and I can serve whoever I want however I want.

Lesson #4: Consistent Inspired Action Is The Road To Success

Choosing to be your own boss means you will need to consistently take action towards making your vision a reality. You’ll also need continual inspiration to stay true to your vision as you progress. 

Taking consistent inspired action doesn’t mean doing a bunch of stuff daily. It means taking strategic actions toward building your social venture over time. Consistent actions that will help you and your organization level up. 

That might look like working on strategies to grow your brand or developing and marketing new products or services. When you take consistent inspired action you are working with your intuition to guide you on where to use your energy.

You Have to Ask Yourself “What Have You Done to Make It Happen, Boss?”

Growing your organization will require a lot out of you. Your time, energy, and attention will have to be dedicated to what you are trying to accomplish. 

In order to do that, you also have to focus on yourself so you can have a consistent pool of energy to take the inspired actions necessary for sustainable success. 

Part of the mindset coaching for female entrepreneurs that I focus on is how to show up for your business or non-profit if you are the founder or leader. 

That means asking yourself what you are willing to do to make it happen. To make sure that you will be successful and you will not fail. 

Fear of failure is one of the biggest barriers that many of my clients face. They don’t start because they don’t want to try and fail. 

Building your own business or nonprofit means that you will have to put yourself out there in ways that may make you uncomfortable. 

You may have to compete with larger corporations that have millions of dollars for marketing and resources you don’t have. To be competitive you may need to do things you don’t know how to do or don’t feel you’re good at, like public speaking or creating videos on social media. 

The important thing is to keep your foot on the gas and keep moving forward to learn the things you need to learn and grow in ways that you never thought possible. 

Lesson 4: You May Experience a Turbulence in Your “Salary” Transitioning from Employee to Boss

Sometimes the road to being your own boss isn’t linear and you have to detour back to “employee” status for a bit. That can be mentally and financially challenging. 

When you’re self-employed you may not make on average the same as what you made as an employee of another organization. You might make less or a lot more.  

The earning potential is one of the things that draws people to entrepreneurship. Unfortunately, if you have to go back to working for someone else and you have a gap in earning or employment while you started your business… you might have some explaining to do. 

If this happens you can list your business on your resume so there is no time gap and shows you were self-employed. You can also try to negotiate other benefits like time off or a flexible schedule that will help you feel at ease if they are not willing to pay you what you made before. 

You can also keep looking and negotiating until you find a company that will pay you what you’re worth. This is my preferred option because I really believe that people should not be penalized for trying entrepreneurship. I’m also a fan of paying people what they are worth.

Lesson #5: Are You a Hunter or a Gatherer?

If you build your own organization, you might notice that you look at earning money differently from others. That might include how you approach sales or fundraising or the time when you choose to solicit funds vs. chill. 

You might be more of a gatherer who is consistently looking for recurring income. Maybe through multiple funding sources or smaller efforts being gathered into a larger pot. 

You might be more like a hunter who waits for a large opportunity and then chooses to hang out and chill until it’s necessary to hunt again. Then you’ll keep repeating this cycle because you’re comfortable with the thrill and chill nature of this approach. 

Neither one is right or wrong, but you might want to know how you approach money before you decide to become your own boss and solely responsible for your wellbeing and survival. 

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Lesson #6: You Get What You Negotiate

When you are working for yourself, everything is a negotiation process. Transitioning from employee to boss with decision-making power means negotiating is a big deal. 

As a social entrepreneur, you have a number of talents that can be offered as services or products. Some of those things might not be your “favorite things to do” but you could make them a revenue stream.  

Being the boss means you have to decide where energy and resources are going to be dedicated in order to get the returns you want (impact & $). That also puts you in the place where you balance fairness, your worth, and market forces (supply/demand/competitor’s offers).

Yep, if you went to college and you’re thinking “I should have paid more attention to economics”… you’re in the right place. All that “econ stuff” is interesting when you overlay impact and the ways that you can leverage your impact to influence market forces. 

My dad would always tell us “I’m the boss”, yet now as adults, we often tell him no we’re in charge. Transitioning from employee to boss means yes you have the title but you also have the negotiation mojo to make this whole thing happen. (Or not. Sad face.)

Lesson #7: Don’t Be Afraid Of Unconventional Lead Gathering

Traditionally coming from the funding and program management perspective, my experience downplayed the role of marketing in building successful ventures. It’s not something that a lot of people know about. I’ve been fortunate enough to work with teams from various consulting firms that specialize in this work. 

When I combine the lessons I learned from my colleagues with what I’ve learned through my business, there are a few things common:

  • Don’t be afraid to stand out and be seen, 
  • Dare to be different, and 
  • Make sure to share how you’re helping others
  • Don’t be the best-kept secret

As the boss of your social venture, these tips can help you get the leads you need to be successful. You have to think outside the box to figure out what actions will link you to the people who need you. Whether that’s clients, customers, funders, or donors… all of those audiences will take work for you to locate and “convert”. 

You also have the opportunity to explore untraditional avenues to locate your audiences and ideal customers/clients/donors/etc.

For example, if you’re designing websites for nonprofit organizations have you looked up the local ones near you and offered to redesign their website to be more efficient at reaching donors and clients? 

Or if you’re the nonprofit wondering why you don’t have clients for your amazing program, have you looked at your ‘sales page’ where you tell them why they need you? 

Finding people who care about the things we care about is how we locate each other, those of us who want to help and elevate. 

We have to use both the conventional and unconventional ways to connect so we can support each other and “buy from within”. Meaning having socially conscious businesses and nonprofits supporting each other in communities throughout the world. 

Last thoughts…Dump the Money Trauma & Make What You Want

An increasing number of social entrepreneurs are emerging and choosing to become their own bosses. The great resignation means that many people are looking to bring their passion + their purpose together in a meaningful way. 

For people who are from black and brown communities, this is a huge deal. We need to support and lift up the BIPOC community of social change creators so they can be successful at leading all of us to change the world. 

Money trauma and the ways that black and brown communities are unable to or uneducated about accessing wealth is a huge weight holding many people back. Unlocking generational health and wealth for people of color will take a lot of help from our communities and allies. 

Lack of capital to start businesses or the inability to locate donors from communities that are not wealthy can hold social entrepreneurs back from sharing their passion and purpose. Supporting the people who are taking the risk to jump from employee to boss is one way you can contribute to making the world a better place.

If you are thinking about taking this journey and becoming your own boss, know that it is what you choose to make of it. You’re in charge of your story and journey, only you have the power to jump in the driver’s seat of your very own sports car and ditch the employee bus. (all risk assumed by you, of course, we’re not liable for your outcome.)

Thank you!

This post was inspired by a conversation in the Social Impact Level Up Club on the Clubhouse App. Follow the podcast for more conversations like these.

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