Tonislava Docheva

Feeling Guilt - The “I Should be..” Syndrome of Entrepreneurship

Yesterday I experienced something new on the entrepreneurial journey and that was feeling extreme guilt. The situation : it was a beautiful and sunny day in San Francisco and I was meeting a friend for lunch to catch up. I hadn’t seen her in 3 months since my leave for Buenos Aires and there was so much going on in our lives that we talked through lunch and decided to spend the rest of the day together to really reconnect.

The moment we decided to go for a movie, I felt a wave of guilt wash over me as my mind scanned all of the emails that would go unanswered. 

By the end of the day, we were having dinner on one of the rooftop bars in the Mission, watching a sunset as we snacked on guacamole and ceviche. Instead of enjoying that beautiful moment with my friend, all I could think about is “I should be answering those emails. I should be setting up meetings this week. I should be, I should be, I should be!” This train of thought totally took me out of the present moment and I felt like I was doing a disservice to my relationship with my friend because I simply couldn’t be present with her. And then of course the GUILT!

Later that night I reflected on my feelings of guilt which had only grown stronger. I tried to dig deeper and find out the source of that guilt and I realized I was creating an image in my mind of what I thought the priorities of a true entrepreneur should look like. In my mind, the business came first but in this situation I had chosen to focus on my relationship.

I felt like I was betraying myself and the entire entrepreneurial journey that I had undertaken - I felt like a fraud, I felt like I had failed myself and my company. 

After that whole scenario played out in my head I gave myself a big REALITY CHECK. 

A few unanswered emails does not mean my company is going to fail.  Taking a day to focus on an important relationship in my life is crucial for my wellbeing and gives me grounding and balance which is crucial to my personal and professional success. I realized that by nurturing my relationships, I feel more inspired and motivated to work on my company. This immediately made that heavy and horrible feeling of guilt lift and I felt ready to tackle those unanswered emails … the next day!






Follow your Fear to Success

Ok so maybe you’ve had your breakthrough entrepreneurial vision for what you want to create or have a business idea that’s been on your mind and you’ve committed yourself to it. Although there’s lots of excitement, these first stages of entrepreneurship are also undoubtedly filled with fear, doubt, and sometimes the most crippling - procrastination. 

Although the entire entrepreneurial journey is filled with doubts and unknowns - they are not quite as strong as in the first stages when you are the farthest away from your destination - or at least that’s what it feels like.

On those darker days when self-doubt, lack of motivation, procrastination and fear come storming in try to remember: 

Don’t run away from what you fear - follow it instead.

Fear has a sneaky way of perceiving everything that is unknown as something that will be life threatening to you. This can be totally crippling when you are embarking on an entrepreneurial journey where EVERYTHING is the unknown. 

I was first introduced to this concept in the book Big Magic - Creative Living Beyond Fear by Liz Gilbert where she says:  

“Fear is always triggered by creativity because creativity asks you to enter the realms of uncertain outcome and fear hates uncertain outcome.” 

When I began my entrepreneurial journey, fear would keep me from moving towards my dreams when I would go to write my business plan or attend a networking event. In those moments, I had to make a choice - Let fear hold me back or see what would happen if I went straight towards it. 

Well - let me tell you, amazing things started to happen. That one networking event I was so afraid of going to created incredible opportunities for me and all I really had to do was follow that insistent fear all the way to the door. Similarly, sitting down to write the draft of my business plan created immense clarity in my mind that allowed me to actually set goals and expectations for myself. 

When fear starts to feel overwhelming and all consuming we have to remember that it is our body’s defense mechanism against threats and that it can’t distinguish between a real life-threatening situation and one where we are simply doing something that we haven’t done before. 

So next time you realize that fear is holding you back from where you want to be - take it by the hand and say “we’re going there.” 



Anna Dostoyevskaya - Russia’s First Businesswoman and Brand Strategist

When you search Anna Dostoyevskaya online it is without a doubt her famous husband’s name, Fyodor Dostoyevsky, that is the center of attention. Titles like “Anna Dostoyevskaya on the Secret to a Happy Marriage,” and “Writers and their Wives” are amongst a few articles that tell us the significant influence that Anna had on the writer - but there is so much more left unsaid about this creative, entrepreneurial and fierce woman who can teach us the importance of branding and a few keys to business success. 

Anna Dostoyevskaya by Laura Callaghan from the book The Who, The What and The When

From a young age, Anna’s desire was to financial support herself and in pursuit of this she went to college to study stenography (a type of short-hand which was radical during the early 1880’s). At the time, Fyodor was in deepening financial debt and needed to write a book in 26 days. Anna agreed on an arrangement to help him transcribe his dictations using stenography and indeed they achieved the seemingly impossible of finishing the book. He also fulfilled his end of the agreement and payed her 50 rubles or the modern equivalent of $1,500. 

However, by the end of their time working together, Fyodor had fallen deeply in love with Anna - her independence, disciplined work ethic, and most of all her empathetic understanding of him. She too had grown to love the once miserable writer who seemed transformed by her. In due time, the two were married and living together in pure bliss, but Fyodor’s financial instability was still burdening the family - Anna decided to take matters into her own hands. 

“She single handedly revolutionized the publishing industry and brought her family out debt by turning her husband into Russia’s first self-published author.”

To achieve this she meticulously studied the current publishing industry, researched vendors and distribution channels, and created a personal brand around Dostoyevsky as a national writer and philosopher that is still relevant to this day. 

Anna Dosteoyevskaya is a true entrepreneurial woman with a drive for independence, a strong belief in the power of personal branding, and most of all a love and passion that drove her to these successes. 


Feeling inspired? Want to strengthen your personal brand and message to reach personal success? I can help - TAKE A LOOK 

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