The Road Less Traveled: Don’t Be Afraid Of The Dark

Many entrepreneurs go through The Darkness - eating instant ramen, crashing in their parents' basement, remortgaging their house, fearing monthly cable bills or paying rent  -- before The Big Success Break, as do many who seek a transition to an alt-path.  

While not all alternative legal careers involve entrepreneurship (though in later blog posts we'll speak with lawyers turned entrepreneurs), when it comes to our careers, we are our own entrepreneurs.  We are companies of one.  We are selling our labor and skills and that unique bit of ourselves that only we can offer.  We are convincing others to invest time, money, capital, and goodwill in us.  

What is The Darkness? 

The Darkness is what we experience before The Big Success Break.  We may embrace the uncertainties at first, all fear is the mind-killer, yada, yada. But, sometimes, we found ourselves in The Darkness for a much longer time period than we expected. 

The Darkness comes in the form of hundreds of rejection letters, unreturned phone calls, job interviews that never pan out.  The disappearing numbers in your checking account that seem to reappear on the scale.  The finality of the word 'NO'. 

The Darkness is coming tantalizingly close to The Big Success Break - that final round of interviews, the meeting with that one investor, that life-changing deal that allllmost closes - before the womp-womp of all womp-womps wallops you in the jaw and sets you back to Ground Zero again.  

Like entrepreneurs, those committed to taking the risk of a career change to an alt-path need to be prepared for The Darkness.  


  1. You won't get those twice-a-month cash infusions from BigLaw or BigCorp.  How long can you survive without a salary if you choose to make a leap without anything firm in hand? 
  2. You're not on the career conveyor belt anymore, so ticking the boxes of regular promotions or raises may not apply to your current or future reality.  
  3. You may find yourself questioning whether an alt-path is the right one: if you're single, your social life may dwindle. If you're not, you have to weigh whether or not anyone is depending on your income and earning power against your decision to go alt
  4. You may have to re-evaluate your definition of success. 

Earlier in January, I spoke as a panelist for NYSBA's Career Development Conference on the panel entitled Back In Practice: Returning To The Legal Profession. The event was hosted by NYSBA's Lawyers In Transition committee, which makes it germane to anyone considering a transition on or off an alternative legal career path.

A webcast of the panel can be found here.  I start speaking at approximately 7 minutes in.  

At 1:00:36, a member of the audience asks a question about The Confidence Gap as applied to the frustrations of changing career paths.  You can view my response to the question at 1:02:48, which details some of my own career-change struggles, as well as those of lawyers I know and have worked with.  While shepherding hundreds of attorneys through a career change, I've seen this confidence drop (and experienced it myself) firsthand. The question on The Confidence Gap made me think of my time in The Darkness, and what I did to escape it. 

Why is The Darkness relevant for anyone seeking or experiencing a career change?  

If we're in transition, we've likely just experienced a shock to the system, both in a professional and existential sense.  Many of us don't have linear career paths, but as a culture, Americans almost fetishize individual success.  One of our country's enduring myths is Horatio Alger. Our "American Dream" involves the idea that we will leave this world in markedly better circumstances than the ones in which we entered it.  

Still skeptical?  Just scroll down your social media feed. What do you see?  Success, all around. Just now, on my daily scroll, I spy the following humblebrags (and I'm guilty of more than a few): 

  1. Happy couples or groups of friends vacationing somewhere much more enticing than my current location, or wearing outfits more on trend than anything in my closet, or eating artfully plated dinners (okay, I'm guilty of this last one) and sipping tasty libations (guilty of this one, too). 
  2. A smattering of one-ring-to-rule-them-all engagement shots
  3. Smiling, well-behaved, well-dressed children in suspiciously clean living rooms.
  4. Instagram profiles of someone's new jewelry line or yoga studio or lifestyle blog.  
  5. People fresh from their daily exercise regimens. Look at those abs! Those legs!  They're sexier than Pope Jude Law. 

But bear this in mind - behind every snapshot of success is a long tunnel of backstory featuring The Darkness in a starring role.  

Seeing people's successes without knowing what it took them to get there can be some toxic bull**** for anyone. It can be even worse if you're going through The Darkness, so avoid the comparison trap, or, even better, abstain from social media until you're out of The Darkness. 

I'll leave you with some final questions: What was the last major risk you took? What were the consequences of that risk?   


Alexis Lamb is a recovering lawyer who served time as a transactions associate in the New York office of O'Melveny & Myers and the Hong Kong office of Linklaters. She is currently Associate Director of Talent at Bliss Lawyers.   

Connect with Alexis at:

Write a comment

Please login to comment

Remember Me

Become a Member

FREE online community for women in the legal profession.



Subscribe to receive regular updates, news, and events from Ms. JD.

Connect with us

Follow or subscribe