Using even difficult experiences to find clarity on what matters to her has helped Jamie Lieberman build a career and life she loves.
Using experience to develop career clarity and autonomy
Jamie Lieberman is a practicing attorney of 15 years, podcaster, and entrepreneur dedicated to making legal stuff accessible to entrepreneurs and to sharing the message that legal stuff does not have to be scary. As the owner and founder of Hashtag Legal, she leads an all-female virtual team focused on providing clients with advice on a wide range of subjects such as intellectual property, contracts, privacy, FTC and general business law as well negotiation strategies. Aside from her professional endeavors, Jamie is the wife of another lawyer and mom to two active boys.
Not long after her first son was born, she came to the realization that it would be challenging to see her son and practice law in the traditional sense. She refused to accept that it was impossible to do both, and that is where her own practice was born. While launching her practice, she had her second son.
Her team and staff are all women with flexible schedules to enable them to enjoy family lives, personal lives and have balance.
She got her start in the influencer space when she started to freelance after leaving her job working for the U.S. federal government. Her freelance work started off as writing briefs for other attorneys using her background as a litigator. At the same time, she was running her own blog, writing about life in NYC and later, parenting. When she started this endeavor seven years ago, the word “influencer” didn’t even exist in the social media world, and bloggers were just starting to make businesses out of their blogs.
About 6 years ago, Jamie was working for a company that ran conferences for bloggers, writing about legal and non-legal matters. One day, the owner of that company approached her and asked if she would give a talk about legal issues for bloggers. After the talk, several bloggers approached her and asked for help because they were struggling to find lawyers who understood the blogging business. That is how her practice was born.
As she worked with influencers, agencies, and brands, she realized there was a natural extension of her work into designers, creatives, online professionals, app developers, service professionals, which then turned into entrepreneurs. This area was very underserved by lawyers. Jamie saw this opportunity and structured her legal services so that clients are not intimidated by them. She and her team are transparent in their costs and have open communication. She is able to empathize in her clients’ experiences because she had run and sold other businesses.
She got clarity on the type of law she wanted to practice based on a podcast she was on called “The Happy Lawyer.” The host of this podcast asked her, “Is it the work, or is it the client?” She realized it was her clients that got her up every morning. It’s the counseling and helping people that is her driving force, not just in her career, but in life in general.
Her experience of running her own practice was completely the opposite of working for a large law firm or the government. In the latter, there was very little room for creativity because things were simply done a certain way. There was no opportunity to distinguish yourself or do anything that would change the way a project was viewed. Having no autonomy was stifling for Jamie. She wouldn’t take back her experience for anything, though, because it was through this experience that she was able to figure out that autonomy is very important to her.
A typical day
Jamie tends to stay up very late and starts her day at 7 am. By 8, everyone is ready to leave – her kids go to school, her husband goes to work (he is also an attorney), and Jamie goes to the gym. This means she starts her workday a little later, but the hour at the gym is her “me-time.”
Once she’s back home from the gym, she works for most of the day. Her kids come home around 5:30 pm, at which point she stops working. The 2 hours that she spends with them as soon as they come home are important to Jamie. She talks about their day with them, helps them with homework, eats dinner, and puts them to bed by quarter to 8. Around 9 pm, she picks up her laptop again and works until midnight. She goes to bed somewhere between midnight and 1 am.
Jamie’s weekends are usually based around her family. Depending on the time of the year, Jamie and her family will either walk or bike to the farmer’s market, go to the park, hang out with friends, go swimming, or go across the Hudson River into Manhattan. She does occasionally work if she has a deadline to meet that she hasn’t been able to get around to during the week. She’s working to get out of the habit of answering emails on the weekends.
In the past, Jamie’s default answer to every request was yes, but now it’s no. When she is invited to participate in something, saying no forces her to think, “If I take this on, is it worth the time that I’m spending because it’s going to have to replace something else.” That something else can be something as simple as relaxing. Finding time is hard enough as it is, so Jamie has to think hard about every opportunity that is presented to her. Sometimes, it’s a very easy yes. Other she finds herself thinking for too long; she’s learned there’s a reason for that hesitation, and she follows that instinct to a no.
Biggest Productivity Challenges
Organization and time management are Jamie’s biggest struggles. That’s why her first hire in her practice was a Director of Operations. She relies on the people around her and a variety of apps and tools to help her achieve all that she does.
The Bullet Journal has been tremendously helpful for her.
She heavily schedules her day to a point where other people would cringe so that she can keep herself on track. She uses Google Cal and Fantastical.
Time blocking is an important tool for Jamie. For example, she’ll answer email from 10-11 am, finalize a project from 11 am-noon, block off 1-4 pm daily for phone calls, and do client legal work at night when it is quiet.
Tools Jamie recommends
Jamie uses Dubsado in her business. It is a CRM and project management tool which her Director of Operations manages. For time-keeping, conflict checks, and billing, she uses Clio. Acuity is another important tool for Jamie that has automated her scheduling.
Her team members have a lot of autonomy. They have set office hours, but it doesn’t matter what that office looks like; they can be on the beach if that’s what works for them. If they have to step out to take care of some personal matters, she is told about it but not asked, which is very important to Jamie. Her team is loyal, productive, and they put in extra effort because she isn’t looking over their shoulder, and she gives them the power to do what they want to do and to be the best at what they want to do.
Jamie and her husband share a grocery list (Our Groceries app) as well as a calendar, so they send each other calendar invites when they have events to attend.
Jamie’s family relies on mostly technology-based tools with a little bit of analog mixed into it. They have a big chalkboard calendar that sits in the kitchen. At the end of every month, they all sit around and talk about what they did that month before they erase it for the next month. They also talk about what’s coming up, where mom and dad are going on business trips, things to look forward to, etc.
What happens on a day when everything gets away from you?
When things happen, Jamie steps away, even if it’s only for half an hour, to take time for herself. She writes, takes a walk around the block, drinks a cup of coffee in silence, or uses her meditation app to “calm her body.” Then she puts her shoulders back, and tells herself, “You’ve had your half-hour. Time to go back and do the best you can.” Sometimes, when you’re not having the best day, you just gotta put it down and say “I’m going to come back to it tomorrow when my head is clearer.”
What’s on the horizon for Jamie?
At the time of recording, Jamie was very much looking forward to her beach trip with her family. In the fall, she has some speaking engagements come up.
Last thoughts on making a life that matters
Trust your gut. You probably already know the answer. You are really really smart, and you know what is best for you. Silence the noise of everybody else’s opinions or the ‘should haves.’ It should be the ‘I wants.’
What do you think?
Connect with Jamie
More about Jamie
Jamie Lieberman is an attorney, podcaster and entrepreneur dedicated to making legal stuff accessible and to sharing the message that legal stuff does not have to be scary. As the owner and founder of Hashtag Legal, Jamie draws on her experience working with influencer marketing professionals, creatives and business owners to help her clients grow and protect their businesses.
She leads an all-female virtual team focused on providing clients with advice on a wide range of subjects such as intellectual property, contracts, privacy, FTC and general business law as well as negotiation strategies. Jamie is a highly experienced speaker and is the co-host for the FearLess Business Podcast.
She is married to a fellow attorney and has two crazy boys, going into kindergarten and third grade, who keep her very busy outside of work. She loves to travel, read, and work out. Her happy place is the beach and they spend as much time at the Jersey shore as possible.
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