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My Career Shift: What I've Learned After Eight Months

5 tips for anyone hoping to start a business in midlife

By Marla Persky

5 tips for anyone hoping to start a business in midlife

When Next Avenue was kind enough to feature me in January 2014 (“Inside the Career Shift of a Star Corporate Lawyer”), I had just retired as General Counsel of a large multinational pharmaceutical company and made a conscious decision to leave the law so I could start two companies. I wanted to spend my time and energy doing things about which I was passionate.

One of the businesses is WOMN LLC, a consulting firm dedicated to helping women succeed in the business of law. The other is Epicurean Travel, which arranges tours to select destinations for people who enjoy the intersection of food, culture and history.
(MORE: Turning Your Passion Into a Career)

These first eight months have been a combination of wonderful and frustrating, with plenty of surprises. Along the way, I’ve learned five things that might be helpful for anyone else considering becoming an entrepreneur as a second act:
1. Don’t bite off more than you can chew. I thought that starting two businesses simultaneously, albeit in two vastly different fields, would be doable. After all, I’d juggled dozens of projects at the same time throughout my career and had been very successful in prioritizing and managing my time. But I underestimated how long it would take me to do things on my own. 
I used to have a team of people to help me accomplish tasks…now there is just me. (Well, actually, I have partners in both businesses and they are a great help, but most of the burden still falls on me.) 
Establishing new destinations for Epicurean Travel has taken much longer than I anticipated. And my expansion plans to offer long weekend trips to select U.S. destinations has been more complicated than I anticipated. Arranging those trips is easy — making money, not so much.
With WOMN LLC, because I was feeling overextended, I’ve postponed plans to start a chapter in Chicago and am focusing instead on just the northeast region (from Philadelphia to Boston, but especially New York City). 
By adjusting my expectations, I’ve taken pressure off myself. This has helped me be confident that everything I’m doing is of the highest caliber, which, in turn, increases my happiness.

(MORE: What Successful Entrepreneurs Wish They'd Known Sooner)
2. Flexibility is essential. When you’re starting your own business(es), I’ve found, it is a mistake to be rigid about your plans.
I thought I knew which products WOMN LLC would offer. Then I learned that my potential clients were interested in other things.
I started out intending to help law firms and women in private practice. But in the past few months, I’ve had wonderful opportunities to assist general counsel at companies on projects for their in-house legal departments as well. Since I was a general counsel for over a decade, this is a natural fit — and in some ways an easier “sell” to clients.
So my business models have been morphing, probably for the better. 
A wise friend who has had her own legal industry consulting business for years advised: “Let the customer define what you do.” I know that flies in the face of Harvard MBA rules to “make the market,” but for start-ups — especially service businesses like mine — the low hanging fruit is giving the customer what they want, as long as you don’t overextend yourself or overpromise. 
As a fledgling entrepreneur, I am establishing my credibility and it only takes one misstep to break trust. So although I am broadening what I offer as a consultant, I’m also being very deliberate about how, when and what I can deliver. 

(MORE: Change Careers With the 'Sugar Grain' Principle)
3. There are only 24 hours in a day and work shouldn’t take up all of them. Starting out, I failed to realize that my Type A personality would compel me to either work constantly (my home office is always there) or to feel guilty about not working. To deal with this, I have tapped into my prioritization skills.
By making my family and me my number one priority, I help overcome the clarion call of “work.” 
One reason I retired was to make time to do things I care about. I have aging parents, my 25-year-old daughter lives halfway across the country, my friends are scattered across the world, I have two new dogs who need training and attention and a loving husband who also retired from the practice of law and is now a historical researcher and author.
I have realized, perhaps more acutely than before, that being a well-rounded person is critical to me. But trading one high-pressure career for another (okay, two) does not help one be well-rounded.
To counter that, I now make sure to plan luncheon dates with friends and get away from my office. I go to Florida every six to eight weeks to see my aging parents and to Chicago once a quarter to spend time with my daughter.
My businesses are important to me, but they are not the most important things in my life. The key, I now see, is to give myself permission to make time for my priorities.
My sense of self has shifted. I’m working hard, but my businesses do not define me.
4. Taking risks is different at a start-up than at a big corporation. I’m not afraid of risk. In fact, that’s one of things that made me successful as a general counsel. But it turns out that mitigating risk in small start-ups isn’t the same as with Fortune 500 companies. 
I’ve learned that small companies can be more relaxed about certain corporate formalities. So I don’t use formal contracts in my consulting business — a letter of understanding is fine — and I operate on a handshake with my country partners in the travel business.
I take calculated, hopefully intelligent risks, perhaps even more now than when I was a general counsel because the stakes are different.
5. Enjoy the journey — it’s more important than reaching the destination. One way to make your learning curve less stressful is to ask for help. Find out what others before you have done. Then, take chances and don’t be afraid to follow your own trails.
You don’t always have to take the fastest, most direct route. Trust me, you miss the beauty of the countryside when you only take superhighways. 
Eight months in, I’m now spending more time doing what I like than what I have to do. I am giving myself permission to say “no” to people and projects that in the past I would have done. 
Am I being selfish? Maybe. But in the end, I think this approach will make me more successful — keeping in mind that I get to define success.
My Businesses: the Present and the Future


So here’s where things stand:
Epicurean Travel now has a new website, a social media presence and a logo. I’ve added Guatemala and Portugal to our original destination (Turkey) and have booked several new trips to Guatemala and Turkey. I hope to break even in 2015; 2014 is a year of investment.
My goal is to get Epicurean Travel slightly profitable and then turn it over to my daughter and niece to run with me as an adviser. 
WOMN LLC is starting to pick up steam. I have several clients and am working on a few projects (some are much different that what I had initially envisioned). The firm also now has a website and I have wonderful partner. I think we’ll be in the black by the end of 2014.
Do I have any regrets about retiring and starting my businesses? No. Do I wish I had started one before the other, for better work/life balance? Yes.
If there’s a Richter scale for happiness, eight months into my career shift, I’m at 7.5.

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