Five Tips to Maintain Your Self-Esteem When You Work for Yourself

“Two roads diverged in the woods and I—I took the one less traveled by, and that has made all the difference.

Robert Frost

There are few better examples of what “taking the road less traveled” looks like in real life than running your own business.

It’s exhilarating and empowering to know that you’re the one calling all the shots, from the all-important decision of what type of entity to set up—sole proprietorship, LLC, S-Corp, etc.—to whether you’d prefer rounded or square corners on your business cards.

It’s quite possible today for nearly anyone to make the leap into self-employment, as all the advice you need about running your own business, particularly from a task-oriented perspective, can simply be googled.

And the perks are sweet.

You don’t have to moderate or compromise your vision, your expectations, your goals for anyone else. You write your own to-do list and set your own appointment calendar. Never mind a lunch hour, you can take a lunch afternoon, or watch Netflix in the middle of a work day.

The drawbacks are well documented as well, especially the cashflow kind of drawbacks. But most people going into business for themselves are quite aware of the cash investment it takes to get a company up and running, and they’ve either made plans for or peace with an uncertain financial future.

So, one might think that ultimately, building your own business would be a shot of self-esteem to the arm. And that is true, at first. Seeing your name on a door, on a card, or in the local paper is thrilling.

But I’ve been running my own businesses now for over 16 years, and I can say that the adrenaline rush wears off. So do the congratulatory words and support from family and friends. And then, you’re alone.

When you’re out there, I mean really out there with only your own sniffer for guidance, there are no regular pats on the back. You’re in the trenches, all by yourself, so there is no one to say, “Good work today.” No one is right there to rave with you over a recent success, or wallow with you through a disappointment.

Because you’re not regularly sharing with others who understand what your work is and what it takes to succeed, your successes start looking smaller, while disappointments loom larger. When there’s no one to remind you where you started from, growth is harder to see.

Much of the advice out there about self-employment is very helpful. But it falls flat in these dark, lonely places, places that revel in taking a good-size bite out of your self-esteem.

So, to go alongside the blogs about where to get the best deal on an office chair, here are five tips about maintaining a sense of self-worth as you walk your own less-traveled path.

  1. Celebrate the small wins.


For my own survival and sanity, I have made it my practice to not wallow in the nos that inevitably come when you’re self-employed, but to turn right back around and try again. I think it’s an overall healthy habit, equivalent to the “get back on the horse” advice.

But a couple weeks ago, on a Sunday afternoon, I finally got a yes after a long string of nos.

If I were in an office, surrounded by co-workers, I feel like that would’ve been the moment I’d have been met with a few high-fives, maybe even taken out for a celebratory lunch. But without others around to point out my success, it barely registered.

In fact, my survival instinct is so automatic by now, I responded to the yes almost in the same way I would have to a no. “One yes is not enough,” I said to myself immediately after receiving it. “I need to get a second yes, a third yes, a string of yeses!”

But then I stopped, as I realized how quickly I moved the goal posts on myself. Then, I gave myself the afternoon off, and popped open a bottle of wine just a little earlier than usual.

Every small success matters. It matters to the business, but more importantly, it matters to maintaining a healthy mindset.

  1. Outsourcing is not a failure.


Walking down the road less traveled inevitably makes one a jack of all trades, but it does not make one an expert in these trades.

On one hand, there is so much readily-available information out there to do most if not all business-related activity for ourselves, it almost seems as if we should be doing everything.

On the other hand, readily-available experts are out there too, just waiting to help us. There are bookkeepers who will do everything from your quarterly billing to your daily data entry. There are website managers who will maintain your site as often as you need. There are marketers who will charge you by the hour to write emails you could also write yourself.

Recently, in an effort to save money, I opted to design a new website using what I thought were good-enough customizable templates. I spent several days working on it, thinking I was doing quite a good job. But then, I hit a snag as I realized there was functionality I needed but didn’t know how to do.

I reached out to a website designer, who not only agreed to help me with the new functionality but sold me on letting her re-design the entire thing. I agreed, but wondered how much better the site could really be from what I’d already accomplished.

As it turns out, quite a lot better. Also, as it turns out, I’m not a great website designer. But this is not a problem (unless, of course, my business was website design). Not as long as I accept the truth that I can’t do it all myself. Outsourcing is not a testament to nor a judgment on our abilities, but rather to our wisdom about knowing when we need help.

  1. Define success on your terms.


“Compare and despair”— that’s what my writing coaches remind us in class. This is particularly good advice in these days of social media, where it is so easy to not ever feel good enough. Something as minor as a Facebook post that gets no likes, or seeing a similar business racking up followers on Instagram can suddenly become reasons to fold up the tent.

But the beauty of being in business for yourself means that you get to decide what success looks like.

Success to you might very well mean becoming a national brand. But it also might mean making just enough money to keep the business afloat. Or, it could be little more than an opportunity to share something you love with more people.

Rather than putting ourselves in competition with others, where we will always find reasons to come up short, only we know what satisfies the itch to have started the business in the first place. Compete with yourself, if that drives you. But always remember that we get to decide what are goals are, and they don’t have to please or impress anyone else but ourselves.

  1. Be your own voice of encouragement.


Years ago, on my first day on a new internship as a computer programmer, my boss showed me a broken program and asked me to fix it. I was overwhelmed just trying to understand what the program did, let alone fix it. Meanwhile, account executives were regularly stopping by my desk, demanding it be done.

At lunchtime, no closer to a solution than at 8:00 a.m., I grabbed my coat and bags and walked into my new boss’s office, near tears, ready to quit.

But he asked me to sit down. He apologized for the mess I walked into, but told me he believed I had the skillset needed to do the work. He also gave me permission to tell anyone stopping by my desk to get lost. He asked if I’d try again.

Refueled, I went back to my desk. I stepped through the code, line by line, until I found and fixed the error. I worked at this company for three more years.

But today, I don’t have a boss like this to turn me around when I feel overwhelmed. So, add it to the list of jobs for a self-employed business owner: we are the ones who have to get ourselves back up after every setback, rejection, and failure. We have to be our own voice of encouragement.

To date, I have talked myself out of quitting so many times that it’s more a joke than an option. It usually takes the form of a meeting with myself, where I remind myself of my value, set boundaries on distractions, and go back to try again.

  1. You are not your business.


One of my favorite businesses I ever created was a yoga studio business nearly a decade ago. For years, I’d been teaching yoga on my own, but I wanted to build something bigger, with more possibilities for growth.

To do so, I needed partners.

But within just a year, it was clear that my vision and my partners’ visions were not in alignment. It was equally clear that I was the one who would have to go. This meant walking away from something I’d helped build from the ground up.

The toll this took on my self-esteem is impossible to measure. My whole identity had been wrapped up in being not only a yoga teacher, but a studio owner. Who was I once that was suddenly and completely gone? I had to do difficult internal work to come to the realization that I was not my businesses, I was not my work, I was not the size of my now non-existent student base.

We are not our creations, only that which creates our businesses. We are here not to force things for our own sake, but to try things, see what happens, manifest what is meant to be manifested, and let go of that which is not.

Neither success nor failure defines who we are. See your work as play. Be in the flow, but do not become attached to the outcome.

Having run my own businesses now for over 16 years, self-creation and re-creation is such a part of who am I don’t know another way of being in the world. I’m so accustomed to walking my own path, that if I had to take a job where I had to follow in someone else’s footsteps, no matter how great those footsteps, I would probably feel stymied.

From my vantage point, for anyone considering taking the road less traveled by opening their own business, I say go for it. The freedom you get in envisioning and creating your own world is invigorating.

But, I would also caution anyone who is thinking about getting into business for themselves to take good care of their self-esteem. It will get challenged. But this too, can be seen as a perk of the job, rather than a drawback.

Because in the process of having my self-esteem so regularly challenged, like a muscle, it’s actually grown stronger, more resilient, more flexible. And if a stronger self-esteem is the greatest thing to emerge from all my time in business for myself, then I count that as one of my greatest successes.


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